JPH10512248A - 農薬特性を有する4−アリール−及び4−ヘテロアリール−5−オキソ−ピラゾリン誘導体 - Google Patents
農薬特性を有する4−アリール−及び4−ヘテロアリール−5−オキソ−ピラゾリン誘導体Info
- Publication number
- JPH10512248A JPH10512248A JP8521407A JP52140795A JPH10512248A JP H10512248 A JPH10512248 A JP H10512248A JP 8521407 A JP8521407 A JP 8521407A JP 52140795 A JP52140795 A JP 52140795A JP H10512248 A JPH10512248 A JP H10512248A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- formula
- compound
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 239000004009 herbicide Substances 0.000 claims abstract description 41
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract 3
- 230000003042 antagnostic effect Effects 0.000 claims abstract 2
- -1 phenyl Chemical group 0.000 claims description 130
- 239000000203 mixture Substances 0.000 claims description 111
- 239000013543 active substance Substances 0.000 claims description 90
- 229910052736 halogen Inorganic materials 0.000 claims description 68
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 241000196324 Embryophyta Species 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 230000002363 herbicidal effect Effects 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 241000607479 Yersinia pestis Species 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 241000209504 Poaceae Species 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 241000238876 Acari Species 0.000 claims description 8
- 240000008042 Zea mays Species 0.000 claims description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 235000013339 cereals Nutrition 0.000 claims description 8
- 235000005822 corn Nutrition 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 235000013311 vegetables Nutrition 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 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 244000045561 useful plants Species 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- ZVWUREAHHMOESK-UHFFFAOYSA-N 1-phenylpyrrole-3-carboxylic acid Chemical class C1=C(C(=O)O)C=CN1C1=CC=CC=C1 ZVWUREAHHMOESK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 241001024304 Mino Species 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 238000009395 breeding Methods 0.000 claims 4
- 230000001488 breeding effect Effects 0.000 claims 4
- 125000003356 phenylsulfanyl group Chemical class [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 claims 1
- 206010061217 Infestation Diseases 0.000 claims 1
- 241001553014 Myrsine salicina Species 0.000 claims 1
- 241000506319 Trifur Species 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- 239000004020 conductor Substances 0.000 claims 1
- 125000004996 haloaryloxy group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 150000003217 pyrazoles Chemical class 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 20
- 230000000895 acaricidal effect Effects 0.000 abstract description 7
- 239000002917 insecticide Substances 0.000 abstract description 7
- 239000000642 acaricide Substances 0.000 abstract description 5
- 241000894007 species Species 0.000 description 43
- 239000007787 solid Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000002245 particle Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000000654 additive Substances 0.000 description 16
- 239000000839 emulsion Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000000843 powder Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 235000008504 concentrate Nutrition 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000009471 action Effects 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 239000000428 dust Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004546 suspension concentrate Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 230000000885 phytotoxic effect Effects 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000009331 sowing Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 240000002791 Brassica napus Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
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- 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 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- WROZTZHKRRNHBS-UHFFFAOYSA-N phenyl propaneperoxoate Chemical compound CCC(=O)OOC1=CC=CC=C1 WROZTZHKRRNHBS-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
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- 239000008247 solid mixture Substances 0.000 description 1
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- 229960000391 sorbitan trioleate Drugs 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 238000000967 suction filtration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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- 239000003784 tall oil Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical class [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH00108/95 | 1995-01-13 | ||
| CH10895 | 1995-01-13 | ||
| PCT/EP1995/005152 WO1996021652A1 (en) | 1995-01-13 | 1995-12-29 | 4-aryl- and 4-heteroaryl -5-oxopyrazoline derivatives having pesticidal properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10512248A true JPH10512248A (ja) | 1998-11-24 |
Family
ID=4179456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8521407A Pending JPH10512248A (ja) | 1995-01-13 | 1995-12-29 | 農薬特性を有する4−アリール−及び4−ヘテロアリール−5−オキソ−ピラゾリン誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0804422A1 (de) |
| JP (1) | JPH10512248A (de) |
| CN (1) | CN1175248A (de) |
| AR (1) | AR002020A1 (de) |
| AU (1) | AU4435396A (de) |
| BR (1) | BR9600088A (de) |
| CA (1) | CA2210286A1 (de) |
| IL (1) | IL116697A0 (de) |
| MX (1) | MX9705247A (de) |
| TR (1) | TR199600024A2 (de) |
| WO (1) | WO1996021652A1 (de) |
| ZA (1) | ZA96243B (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004537570A (ja) * | 2001-08-10 | 2004-12-16 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 置換環状ケト−エノール系選択的除草剤および毒性緩和剤 |
| JP2012167122A (ja) * | 2005-02-09 | 2012-09-06 | Syngenta Participations Ag | 除草効果がある置換された3−ヒドロキシ−4−アリール−5−オキソピラゾリン誘導体の製造方法 |
| JP5423905B2 (ja) * | 2010-12-02 | 2014-02-19 | 小野薬品工業株式会社 | 新規化合物及びその医薬用途 |
| WO2016039404A1 (ja) * | 2014-09-12 | 2016-03-17 | 公益財団法人相模中央化学研究所 | ピラゾリノン誘導体、その製造方法、及びそれを有効成分として含有する除草剤 |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19808261A1 (de) | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| RO120911B1 (ro) | 1998-03-13 | 2006-09-29 | Novartis Ag | Derivaţi de 3-hidroxi-4-aril-5-oxopirazolină, activi ca erbicide |
| DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE19818732A1 (de) | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| WO2000047585A1 (en) * | 1999-02-11 | 2000-08-17 | Novartis Ag | 3-hydroxy-4-aryl-5-pyrazoline derivatives as herbicides |
| US7915199B1 (en) * | 1999-09-07 | 2011-03-29 | Syngenta Crop Protection, Inc. | Herbicidal composition |
| CN1272324C (zh) | 1999-09-07 | 2006-08-30 | 辛根塔参与股份公司 | 新颖的除草剂 |
| HUP0202813A3 (en) * | 1999-09-07 | 2003-10-28 | Syngenta Participations Ag | Herbicidal composition |
| RU2262846C2 (ru) * | 1999-09-07 | 2005-10-27 | Зингента Партисипейшнс Аг | Гербицидная композиция, способ борьбы с сорными и травянистыми растениями |
| MXPA04007745A (es) * | 2002-02-13 | 2004-10-15 | Syngenta Participations Ag | Composicion herbicida. |
| AR042282A1 (es) | 2002-12-05 | 2005-06-15 | Syngenta Participations Ag | Proceso para la preparacion de dinitrilos de acido fenilmalonico |
| DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
| DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
| DE10331675A1 (de) | 2003-07-14 | 2005-02-10 | Bayer Cropscience Ag | Hetarylsubstituierte Pyrazolidindion-Derivate |
| DE10337497A1 (de) | 2003-08-14 | 2005-03-10 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-Pyrazolidin-3,5-dion-Derivate |
| DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
| DE102004035133A1 (de) | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern |
| DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
| DE102005059469A1 (de) | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
| DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
| CN101580489B (zh) * | 2008-05-14 | 2011-07-20 | 中国中化股份有限公司 | 含氮杂环化合物及其制备与应用 |
| GB0900641D0 (en) | 2009-01-15 | 2009-02-25 | Syngenta Ltd | Novel herbicides |
| GB0901086D0 (en) | 2009-01-22 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901835D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901834D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| BRPI1008949B1 (pt) | 2009-03-11 | 2018-07-10 | Bayer Intellectual Property Gmbh | Cetoenóis haloalquilmetilenóxi-fenil-substituídos e seu uso, composição, seu uso e seu método de produção, métodos para combate de pestes animais e/ou crescimento de plantas indesejadas |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| UA113753C2 (xx) | 2012-01-26 | 2017-03-10 | Фенілзаміщені кетоеноли для боротьби з паразитами риб | |
| WO2014142308A1 (ja) * | 2013-03-15 | 2014-09-18 | 公益財団法人相模中央化学研究所 | 二環性ピラゾリノン誘導体及びそれを有効成分として含有する除草剤 |
| BR112015023270A2 (pt) * | 2013-03-15 | 2017-07-18 | Kaken Pharma Co Ltd | derivado de pirazolinona policíclico e herbicida compreendendo o mesmo como componente efetivo |
| CN114554845B (zh) | 2019-07-18 | 2024-06-18 | 安道麦阿甘有限公司 | 包含除草剂的稳定制剂 |
| CN115720487B (zh) | 2020-04-06 | 2025-10-14 | 安道麦阿甘有限公司 | 抗氧化剂和活性成分的共晶及抗氧化剂作为稳定剂的用途 |
| CN114106016B (zh) * | 2020-08-29 | 2025-08-12 | 海利尔药业集团股份有限公司 | 一种苯基吡唑啉衍生物或其盐、组合物及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4985063A (en) * | 1988-08-20 | 1991-01-15 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-diones |
| DE4109208A1 (de) * | 1991-03-21 | 1992-09-24 | Bayer Ag | 3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate |
| DE4413669A1 (de) * | 1993-07-05 | 1995-01-12 | Bayer Ag | Substituierte Aryl-ketoenolheterocyclen |
-
1995
- 1995-12-29 AU AU44353/96A patent/AU4435396A/en not_active Abandoned
- 1995-12-29 CN CN95197652A patent/CN1175248A/zh active Pending
- 1995-12-29 MX MX9705247A patent/MX9705247A/es unknown
- 1995-12-29 CA CA002210286A patent/CA2210286A1/en not_active Abandoned
- 1995-12-29 EP EP95943223A patent/EP0804422A1/de not_active Withdrawn
- 1995-12-29 WO PCT/EP1995/005152 patent/WO1996021652A1/en not_active Ceased
- 1995-12-29 JP JP8521407A patent/JPH10512248A/ja active Pending
-
1996
- 1996-01-08 IL IL11669796A patent/IL116697A0/xx unknown
- 1996-01-11 AR ARP960100968A patent/AR002020A1/es unknown
- 1996-01-12 TR TR96/00024A patent/TR199600024A2/xx unknown
- 1996-01-12 BR BR9600088A patent/BR9600088A/pt not_active Application Discontinuation
- 1996-01-12 ZA ZA96243A patent/ZA96243B/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004537570A (ja) * | 2001-08-10 | 2004-12-16 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 置換環状ケト−エノール系選択的除草剤および毒性緩和剤 |
| JP2012167122A (ja) * | 2005-02-09 | 2012-09-06 | Syngenta Participations Ag | 除草効果がある置換された3−ヒドロキシ−4−アリール−5−オキソピラゾリン誘導体の製造方法 |
| JP5423905B2 (ja) * | 2010-12-02 | 2014-02-19 | 小野薬品工業株式会社 | 新規化合物及びその医薬用途 |
| WO2016039404A1 (ja) * | 2014-09-12 | 2016-03-17 | 公益財団法人相模中央化学研究所 | ピラゾリノン誘導体、その製造方法、及びそれを有効成分として含有する除草剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| TR199600024A2 (tr) | 1996-08-21 |
| AU4435396A (en) | 1996-07-31 |
| MX9705247A (es) | 1997-10-31 |
| CA2210286A1 (en) | 1996-07-18 |
| WO1996021652A1 (en) | 1996-07-18 |
| IL116697A0 (en) | 1996-05-14 |
| BR9600088A (pt) | 1998-01-27 |
| CN1175248A (zh) | 1998-03-04 |
| EP0804422A1 (de) | 1997-11-05 |
| ZA96243B (en) | 1996-08-19 |
| AR002020A1 (es) | 1998-01-07 |
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