JPH0369338B2 - - Google Patents

Info

Publication number: JPH0369338B2
Authority: JP; Japan
Prior art keywords: atom; formula; chlorine; fluorine atom; compound according
Prior art date: 1986-02-28
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.): Expired - Lifetime

Application number

JP62045073A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62207250A (ja

Inventor

Dorabetsuku Yoozefu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1986-02-28

Filing date

1987-02-27

Publication date

1991-10-31

1987-02-27 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1987-09-11 Publication of JPS62207250A publication Critical patent/JPS62207250A/ja

1991-10-31 Publication of JPH0369338B2 publication Critical patent/JPH0369338B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 88
229910052801 chlorine Inorganic materials 0.000 claims description 38
125000001309 chloro group Chemical group Cl* 0.000 claims description 38
229910052731 fluorine Inorganic materials 0.000 claims description 37
125000001153 fluoro group Chemical group F* 0.000 claims description 36
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
230000000895 acaricidal effect Effects 0.000 claims description 9
239000000642 acaricide Substances 0.000 claims description 9
239000002917 insecticide Substances 0.000 claims description 9
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 2
239000012752 auxiliary agent Substances 0.000 claims 1
238000012360 testing method Methods 0.000 description 38
235000013601 eggs Nutrition 0.000 description 26
239000000203 mixture Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 19
-1 cyclohexanone Chemical compound 0.000 description 16
238000000034 method Methods 0.000 description 16
230000000694 effects Effects 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
239000000839 emulsion Substances 0.000 description 13
241000607479 Yersinia pestis Species 0.000 description 11
241000256257 Heliothis Species 0.000 description 10
239000002904 solvent Substances 0.000 description 10
241000238631 Hexapoda Species 0.000 description 9
241000256250 Spodoptera littoralis Species 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
241000254173 Coleoptera Species 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000011550 stock solution Substances 0.000 description 6
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical class CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 5
241000238876 Acari Species 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 5
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 5
241000256248 Spodoptera Species 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
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 5
235000015097 nutrients Nutrition 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
241001388466 Bruchus rufimanus Species 0.000 description 4
240000002024 Gossypium herbaceum Species 0.000 description 4
235000004341 Gossypium herbaceum Nutrition 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000012447 hatching Effects 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000002736 nonionic surfactant Substances 0.000 description 4
229920001451 polypropylene glycol Polymers 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
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 3
241000257159 Musca domestica Species 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000003151 ovacidal effect Effects 0.000 description 3
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000255925 Diptera Species 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
241000257162 Lucilia <blowfly> Species 0.000 description 2
241000736227 Lucilia sericata Species 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001414989 Thysanoptera Species 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
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238000006243 chemical reaction Methods 0.000 description 2
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239000000460 chlorine Substances 0.000 description 2
239000007931 coated granule Substances 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
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150000002367 halogens Chemical group 0.000 description 2
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150000002576 ketones Chemical class 0.000 description 2
230000007653 larval development Effects 0.000 description 2
244000144972 livestock Species 0.000 description 2
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150000002828 nitro derivatives Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 2
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239000000344 soap Substances 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
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TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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GDMCUDVUGLJGEZ-UHFFFAOYSA-N 1-(1,1,2,3,3,3-hexafluoropropoxy)-2-isocyanatobenzene Chemical compound FC(F)(F)C(F)C(F)(F)OC1=CC=CC=C1N=C=O GDMCUDVUGLJGEZ-UHFFFAOYSA-N 0.000 description 1
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QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
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AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 description 1
ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical group CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
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FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
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241000074748 Gagrella grandis Species 0.000 description 1
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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101100172132 Mus musculus Eif3a gene Proteins 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
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241000238814 Orthoptera Species 0.000 description 1
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YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000425347 Phyla <beetle> Species 0.000 description 1
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239000011737 fluorine Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
230000001418 larval effect Effects 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
SQPZZIGOGMGFAL-UHFFFAOYSA-N n-[[2,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical class C1=C(Cl)C(OC(F)(F)C(F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F SQPZZIGOGMGFAL-UHFFFAOYSA-N 0.000 description 1
BEIFSCKZJSIKRA-UHFFFAOYSA-N n-[[5-chloro-2-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC(OCC(F)(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F BEIFSCKZJSIKRA-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000002688 persistence Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940113115 polyethylene glycol 200 Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
230000019617 pupation Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003760 tallow Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
244000045561 useful plants Species 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP62045073A 1986-02-28 1987-02-27 ベンゾイルフェニル尿素、その製造方法および該化合物を含有する殺虫、殺ダニ剤 Granted JPS62207250A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH80886		1986-02-28
CH5238/86-6		1986-12-24
CH4617/86-9		1986-12-24
CH808/86-7		1986-12-24

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2341220A Division JPH0669994B2 (ja)	1986-02-28	1990-11-30	アニリン誘導体

Publications (2)

Publication Number	Publication Date
JPS62207250A JPS62207250A (ja)	1987-09-11
JPH0369338B2 true JPH0369338B2 (hu)	1991-10-31

Family

ID=4195666

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62045073A Granted JPS62207250A (ja)	1986-02-28	1987-02-27	ベンゾイルフェニル尿素、その製造方法および該化合物を含有する殺虫、殺ダニ剤

Country Status (3)

Country	Link
JP (1)	JPS62207250A (hu)
MX (1)	MX5413A (hu)
ZA (1)	ZA871433B (hu)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02155A (ja) *	1987-02-04	1990-01-05	Sumitomo Chem Co Ltd	ベンゾイル尿素誘導体、その製造法、その用途およびその中間体
DE3740636A1 (de) *	1987-12-01	1989-06-15	Bayer Ag	Am aromatischen kern und an der seitenkette fluoratome enthaltende alkoxyaniline und deren herstellung
JP4792199B2 (ja) *	2002-10-07	2011-10-12	石原産業株式会社	家屋害虫防除用組成物及び防除方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5289646A (en) *	1976-01-20	1977-07-27	Bayer Ag	New substituted nnphenylln* benzoyllurea and use thereof as insecticide
JPS53141242A (en) *	1977-05-13	1978-12-08	Dow Chemical Co	Substitution product of phenylaminocarbonyllbenzoamide
JPS55104258A (en) *	1979-02-01	1980-08-09	Ciba Geigy Ag	Substituted nn4433bromaryloxyphenyll nbenzoylureaits manufacture and noxious organism repellant containing it
JPS5826858A (ja) *	1981-07-30	1983-02-17	ザ・ダウ・ケミカル・カンパニ−	置換されたｎ‐アロイルｎ′‐フエニル尿素化合物およびその化合物を含む殺虫剤組成物
JPS61257958A (ja) *	1985-03-14	1986-11-15	イステイトウ−ト・グイド・ドネガニ・ソチエタ・ペル・アツイオニ	殺虫活性を有するベンゾイル尿素
JPS61277660A (ja) *	1985-06-04	1986-12-08	Nippon Soda Co Ltd	ベンゾイルウレア誘導体、その製造方法及び殺虫剤

1987
- 1987-02-27 ZA ZA871433A patent/ZA871433B/xx unknown
- 1987-02-27 MX MX541387A patent/MX5413A/es unknown
- 1987-02-27 JP JP62045073A patent/JPS62207250A/ja active Granted

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5289646A (en) *	1976-01-20	1977-07-27	Bayer Ag	New substituted nnphenylln* benzoyllurea and use thereof as insecticide
JPS53141242A (en) *	1977-05-13	1978-12-08	Dow Chemical Co	Substitution product of phenylaminocarbonyllbenzoamide
JPS55104258A (en) *	1979-02-01	1980-08-09	Ciba Geigy Ag	Substituted nn4433bromaryloxyphenyll nbenzoylureaits manufacture and noxious organism repellant containing it
JPS5826858A (ja) *	1981-07-30	1983-02-17	ザ・ダウ・ケミカル・カンパニ−	置換されたｎ‐アロイルｎ′‐フエニル尿素化合物およびその化合物を含む殺虫剤組成物
JPS61257958A (ja) *	1985-03-14	1986-11-15	イステイトウ−ト・グイド・ドネガニ・ソチエタ・ペル・アツイオニ	殺虫活性を有するベンゾイル尿素
JPS61277660A (ja) *	1985-06-04	1986-12-08	Nippon Soda Co Ltd	ベンゾイルウレア誘導体、その製造方法及び殺虫剤

Also Published As

Publication number	Publication date
JPS62207250A (ja)	1987-09-11
MX5413A (es)	1993-10-01
ZA871433B (en)	1987-10-28

Legal Events

Date	Code	Title	Description
2003-10-31	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
JPH0432057B2 (hu)	1992-05-28
CA1136647A (en)	1982-11-30	Phenylureas
JP2747824B2 (ja)	1998-05-06	置換されたｎ−ベンゾイル−ｎ’−２，５−ジハロー４−ペルフルオロアルコキシフェニル尿素、その製造方法及び有害生物防除におけるそれらの使用方法
KR910000252B1 (ko)	1991-01-23	해충방제에 유용한 벤조일페닐우레아의 제조방법
KR900008136B1 (ko)	1990-10-31	벤조일페닐우레아의 제조 방법
EP0231152A2 (de)	1987-08-05	Phenylbenzoylharnstoffe
CA1178612A (en)	1984-11-27	Phenylureas
CA1281741C (en)	1991-03-19	Phenylbenzoylureas
JPH0115502B2 (hu)	1989-03-17
US4555405A (en)	1985-11-26	Carbamic acid esters useful as pesticides
JPH0369338B2 (hu)	1991-10-31
AU613033B2 (en)	1991-07-25	N-benzoyl-n'-trihalo-haloalkoxyphenylureas, their preparation and the use thereof in pest control
JPH021452A (ja)	1990-01-05	ベンゾイルフェニル尿素、その製法および該化合物を含有する有害生物防除剤組成物
HU197877B (en)	1989-06-28	Insecticide, acaricide and ovicide compositions containing phenyl-benzoyl-urea derivatives as active components and process for producing the active components
JPS6084250A (ja)	1985-05-13	しゆう酸アニリド、その製造方法及び有害生物を防除するためのその使用方法
JPS61151173A (ja)	1986-07-09	ベンゾイルフエニル尿素
US5210100A (en)	1993-05-11	Phenylbenzoylureas
GB2098608A (en)	1982-11-24	Phenylurea derivative
CA1180351A (en)	1985-01-02	Substituted p-phenylenediamines
CA1196651A (en)	1985-11-12	Acylamidosulfenylcarbamates for controlling insects
JPH0251546B2 (hu)	1990-11-07
JPH0370697B2 (hu)	1991-11-08
JPS6157545A (ja)	1986-03-24	置換ベンゾイルフエニル尿素、その製造方法及び該化合物を含有する有害生物防除剤
JPS6197254A (ja)	1986-05-15	ベンゾイルフエニル尿素誘導体、その製造方法及び該化合物を有害生物の防除に用いる方法
JPH0225458A (ja)	1990-01-26	ベンゾイルフェニル尿素