JPH07502267A - 殺虫作用のあるフェニルヒドラジン誘導体 - Google Patents
殺虫作用のあるフェニルヒドラジン誘導体Info
- Publication number
- JPH07502267A JPH07502267A JP5509447A JP50944793A JPH07502267A JP H07502267 A JPH07502267 A JP H07502267A JP 5509447 A JP5509447 A JP 5509447A JP 50944793 A JP50944793 A JP 50944793A JP H07502267 A JPH07502267 A JP H07502267A
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- alkyl
- compound
- phenyl
- alkylthio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000749 insecticidal effect Effects 0.000 title claims description 15
- 150000004031 phenylhydrazines Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 35
- 239000002917 insecticide Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 241000607479 Yersinia pestis Species 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- -1 arylo xy Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 241000238876 Acari Species 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 230000000895 acaricidal effect Effects 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- 230000008029 eradication Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000002506 adulticidal effect Effects 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000118205 Ovicides Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000002267 larvicidal agent Substances 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 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 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000194622 Tagosodes orizicolus Species 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 210000003127 knee Anatomy 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 231100000194 ovacidal Toxicity 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- JKOWBWSGMMKFJG-UHFFFAOYSA-N (2-methoxy-5-phenylphenyl)hydrazine;hydrochloride Chemical compound Cl.C1=C(NN)C(OC)=CC=C1C1=CC=CC=C1 JKOWBWSGMMKFJG-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical class ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- OGYBXNHWTBBAKW-UHFFFAOYSA-N 2-bromo-5-phenylaniline Chemical compound C1=C(Br)C(N)=CC(C=2C=CC=CC=2)=C1 OGYBXNHWTBBAKW-UHFFFAOYSA-N 0.000 description 1
- PZVOYRGZHNJDAY-UHFFFAOYSA-N 5-phenyloxadiazol-4-one Chemical class O=C1N=NOC1C1=CC=CC=C1 PZVOYRGZHNJDAY-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
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- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- SFKTYEXKZXBQRQ-UHFFFAOYSA-J thorium(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Th+4] SFKTYEXKZXBQRQ-UHFFFAOYSA-J 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
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- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/02—Compounds containing any of the groups, e.g. thiocarbazates
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- C—CHEMISTRY; METALLURGY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2491—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-N (X = O, S, Se; n = 0, 1)
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- C07C2601/14—The ring being saturated
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Abstract
Description
Claims (14)
- 1.以Fの構造式を有し: ▲数式、化学式、表等があります▼(I)式中 Xはa)フェニル;低級フェニルアルコキシ;フェノキシ;またはベンジル;そ の各置換基が1つまたはそれ以上のハロゲン、ニトロ、低級アルキル、低級アル コキシ、低級ハロアルキルまたはジアルキルアミノで任意に置換されているフェ ニル環;またはb)グループa)の中の1つの置換基とC1〜C4アルコキシ; ハロゲン;低級アルキル;および低級アルキルチオから選ばれた1つまたはそれ 以上の置換基とであり; YはH、C1〜C4アルカノイル、C1〜C4ハロアルカノイル、ジアルコキシ フォスフォリル、アルキルアミノカルボニル、ハロアルキルススルフォニル、ま たはC1〜C4アルコキシカルボニルであり;RはH、C1〜C6アルキル、C 1〜C6アルコキシ、C2〜C6シクロアルコキシ、ハロアルキル、アルコキシ アルキル、アリールアルコキシ、アルケニル、アルキルチオ、アルコキシカルボ ニル、アルキルアミノ、ヘテロアリール、アリールアルキル、ハロアルコキシ、 アリールオキシ、またはC3〜C6シクロアルキルであって; ZはOまたはSであり; Xがフェニルであるときは、Rがアルキルアミノまたはアルコキシカルボニルで はないという制約条件を有する化合物。
- 2.XがフェニルまたはフェニルとC1〜C4アルコシシであり;YがHまたは COCF3であり; RがCF3、C1〜C4アルキル、C1〜C4アルコキシ、またはC3〜C6シ クロアルキルであって; ZはOである 特許請求範囲第1項記載の化合物。
- 3.以下の構造式を有し: ▲数式、化学式、表等があります▼(II)式中 Xはa)フェニル;低級フェニルアルコキシ;フェノキシ;またはベンジル;そ の各置換基が1つまたはそれ以上のハロゲン、ニトロ、低級アルキル、低級アル コキシ、低級ハロアルキルまたはジアルキルアミノで任意に置換されているフェ ニル環;またはb)グループa)の中の1つの置換基とC1〜C4アルコキシ; ハロゲン;低級アルキル;および低級アルキルチオから選ばれた1つまたはそれ 以上の置換基とであり; RはH、C1〜C6アルキル、C1〜C6アルコキシ、C1〜C4ハロアルキル 、またはC3〜C6シクロアルキルであって;ZはOである 化合物。
- 4.Xがフェニルまたはアルコシシであり;RがCF3、C1〜C4アルキル、 C1〜C4アルコキシ、またはC2〜C6シクロアルキルである 特許請求範囲第3項記載の化合物。
- 5.以下の構造式を有し: ▲数式、化学式、表等があります▼ 式中 Xは水素または低級アルコキシであり;RはH、C1〜C6アルキル、C1〜C 6アルコキシ、C2〜C6シクロアルコキシ、ハロアルキル、アルコキシアルキ ル、アリールアルコキシ、アルケニル、アルキルチオ、アルコキシカルボニル、 アルキルアミノ、ヘテロアリール、アリールアルキル、ハロアルコキシ、アリロ キシ、またはC2〜C6シクロアルキルであって; ZはOまたはSである 化合物。
- 6.以下の構造式を有し: ▲数式、化学式、表等があります▼ 式中 Xは水素または低級アルコキシてあり;RはH、C1〜C6アルキル、C1〜C 6アルコキシ、C2〜C6シクロアルコキシ、ハロアルキル、アルコキシアルキ ル、アリールアルコキシ、アルケニル、アルキルチオ、アルコキシカルボニル、 アルキルアミノ、ヘテロアリール、アリールアルキル、ハロアルコキシ、アリロ キシ、またはC3〜C6シクロアルキルであって; ZはOまたはSである 化合物。
- 7.以Fの構造式を有し: ▲数式、化学式、表等があります▼(I)式中 Xはa)フェニル;低級フェニルアルコキシ;フェノキシ;またはベンジル;ま たはb)グループa)の中の1つの置換基とC1〜C4アルコキシ;ハロゲン; 低級アルキル;および低級アルキルチオから選ばれた1つまたはそれ以上の置換 基とであり; YはH、C1〜C4アルカノイル、C1〜C4ハロアルカノイル、ジアルコキシ フォスフォリル、アルキルアミノカルボニル、ハロアルキルススルフォニル、ま たはC1〜C4アルコキシカルボニルであり;RはH、C1〜C6アルキル、C 1〜C6アルコキシ、C2〜C6シクロアルコキシ、ハロアルキル、アルコキシ アルキル、アリールアルコキシ、アルケニル、アルキルチオ、アルコキシカルボ ニル、アルキルアミノ、ヘテロアリール、アリールアルキル、ハロアルコキシ、 アリロキシ、またはC2〜C6シクロアルキルであって; ZはOまたはSである 化合物の殺虫剤として有効である量を駆除を行うべき場所に施すことからなる好 ましくない害虫を駆除する方法。
- 8.特許請求範囲第3項記載の化合物の殺虫剤として有効である量を駆除を行う べき場所に施すことからなる好ましくない害虫を駆除する方法。
- 9.A)以下の構造式を有し: ▲数式、化学式、表等があります▼(I)式中 Xはa)フェニル;低級フェニルアルコキシ;フェノキシ;またはベンジル;ま たはb)グループa)の中の1つの置換基とC1〜C4アルコキシ;ハロゲン; 低級アルキル;および低級アルキルチオから選ばれた1つまたはそれ以上の置換 基とであり; YはH、C1〜C4アルカノイル、C1〜C4ハロアルカノイル、ジアルコキシ フォスフォリル、アルキルアミノカルボニル、ハロアルキルススルフォニル、ま たはC1〜C4アルコキシカルボニルであり;RはH、C1〜C6アルキル、C 1〜C6アルコキシ、C2〜C6シクロアルコキシ、ハロアルキル、アルコキシ アルキル、アリールアルコキシ、アルケニル、アルキルチオ、アルコキシカルボ ニル、アルキルアミノ、ヘテロアリール、アリールアルキル、ハロアルコキシ、 アリロキシ、またはC2〜C6シクロアルキルであって; ZはOまたはSである 化合物の殺虫剤として有効である量と;B)許容される担体 とからなる殺虫剤組成物。
- 10.A)特許請求範囲第3項記載の化合物の殺虫剤として有効である量と;B )許容される担体 とからなる殺虫剤組成物。
- 11.特許請求範囲第5項記載の化合物の殺虫剤として有効である量を駆除を行 うべき場所に施すことからなる好ましくない害虫を駆除する方法。
- 12.特許請求範囲第6項記載の化合物の殺虫剤として有効である量を駆除を行 うべき場所に施すことからなる好ましくない害虫を駆除する方法。
- 13.A)特許請求範囲第5項記載の化合物の殺虫剤として有効である量と;B )許容される担体 とカらなる殺虫剤組成物。
- 14.A)特許請求範囲第6項記載の化合物の殺虫剤として有効である量と;B )許容される担体 とからなる殺虫剤組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US79650691A | 1991-11-22 | 1991-11-22 | |
US796.506 | 1991-11-22 | ||
PCT/US1992/009855 WO1993010083A1 (en) | 1991-11-22 | 1992-11-17 | Insecticidal phenylhydrazine derivatives |
Publications (2)
Publication Number | Publication Date |
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JPH07502267A true JPH07502267A (ja) | 1995-03-09 |
JP2552811B2 JP2552811B2 (ja) | 1996-11-13 |
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JP5509447A Expired - Lifetime JP2552811B2 (ja) | 1991-11-22 | 1992-11-17 | 殺虫作用のあるフェニルヒドラジン誘導体 |
Country Status (22)
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US (1) | US5367093A (ja) |
EP (1) | EP0641316B1 (ja) |
JP (1) | JP2552811B2 (ja) |
KR (1) | KR100235246B1 (ja) |
CN (1) | CN1033699C (ja) |
AT (1) | ATE148104T1 (ja) |
AU (1) | AU670927B2 (ja) |
BR (1) | BR9206803A (ja) |
CA (1) | CA2123885C (ja) |
DE (1) | DE69217085T2 (ja) |
DK (1) | DK0641316T3 (ja) |
ES (1) | ES2097372T3 (ja) |
FI (1) | FI120340B (ja) |
GR (1) | GR3023097T3 (ja) |
HU (1) | HU219189B (ja) |
IL (1) | IL103828A (ja) |
PL (1) | PL171968B1 (ja) |
RO (1) | RO112860B1 (ja) |
TW (1) | TW234075B (ja) |
UA (1) | UA41298C2 (ja) |
WO (1) | WO1993010083A1 (ja) |
ZA (1) | ZA928915B (ja) |
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JP2008537541A (ja) * | 2005-03-03 | 2008-09-18 | ケムチュア コーポレイション | 殺虫、殺ダニ、及び殺菌ニトロメチレン化合物 |
JP2010527362A (ja) * | 2007-05-16 | 2010-08-12 | ケムチュア コーポレイション | 殺有害生物用ジアゼンオキシドカルボキシレート |
JP2013166707A (ja) * | 2012-02-14 | 2013-08-29 | Sumitomo Chemical Co Ltd | フェニルヒドラジン−β−カルボキシレート化合物の精製方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5543404A (en) * | 1995-07-05 | 1996-08-06 | Uniroyal Chemical Company, Inc | Pesticidal phenylhydrazinephosphates |
US5567723A (en) * | 1995-07-05 | 1996-10-22 | Uniroyal Chemical Company, Inc. | Miticidal hydrazine compounds and their intermediates |
FR2754254B1 (fr) * | 1996-10-09 | 1998-10-30 | Rhone Poulenc Agrochimie | Fongicides a groupes hydroximiques et hydrazoniques |
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- 1992-11-17 AT AT92925247T patent/ATE148104T1/de active
- 1992-11-17 KR KR1019940701712A patent/KR100235246B1/ko not_active IP Right Cessation
- 1992-11-17 JP JP5509447A patent/JP2552811B2/ja not_active Expired - Lifetime
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JP2008537541A (ja) * | 2005-03-03 | 2008-09-18 | ケムチュア コーポレイション | 殺虫、殺ダニ、及び殺菌ニトロメチレン化合物 |
JP4796594B2 (ja) * | 2005-03-03 | 2011-10-19 | ケムチュア コーポレイション | 殺虫、殺ダニ、及び殺菌ニトロメチレン化合物 |
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Also Published As
Publication number | Publication date |
---|---|
US5367093A (en) | 1994-11-22 |
HU9401552D0 (en) | 1994-09-28 |
KR100235246B1 (ko) | 1999-12-15 |
JP2552811B2 (ja) | 1996-11-13 |
BR9206803A (pt) | 1995-05-02 |
EP0641316B1 (en) | 1997-01-22 |
HU219189B (hu) | 2001-02-28 |
DE69217085D1 (de) | 1997-03-06 |
CA2123885A1 (en) | 1993-05-27 |
GR3023097T3 (en) | 1997-07-30 |
CN1033699C (zh) | 1997-01-01 |
ES2097372T3 (es) | 1997-04-01 |
DK0641316T3 (da) | 1997-08-11 |
ZA928915B (en) | 1993-08-06 |
DE69217085T2 (de) | 1997-05-28 |
FI942355A0 (fi) | 1994-05-20 |
AU670927B2 (en) | 1996-08-08 |
TW234075B (ja) | 1994-11-11 |
CN1075952A (zh) | 1993-09-08 |
IL103828A0 (en) | 1993-04-04 |
EP0641316A1 (en) | 1995-03-08 |
FI120340B (fi) | 2009-09-30 |
UA41298C2 (uk) | 2001-09-17 |
HUT68639A (en) | 1995-07-28 |
FI942355A (fi) | 1994-07-20 |
ATE148104T1 (de) | 1997-02-15 |
AU3137493A (en) | 1993-06-15 |
RO112860B1 (ro) | 1998-01-30 |
CA2123885C (en) | 2004-03-30 |
WO1993010083A1 (en) | 1993-05-27 |
PL171968B1 (pl) | 1997-07-31 |
IL103828A (en) | 1997-01-10 |
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