CA1237721A - Derives de pyridazinone, leur preparation, et agents fongicides, insecticides, acaricides et nematocides pour l'horticulture et l'agriculture qui les renferment - Google Patents

Derives de pyridazinone, leur preparation, et agents fongicides, insecticides, acaricides et nematocides pour l'horticulture et l'agriculture qui les renferment

Info

Publication number: CA1237721A
Authority: CA; Canada
Prior art keywords: shea; alkyl; denotes; halogen; c4hg
Prior art date: 1982-03-05
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

Application number

CA000422912A

Other languages

English (en)

Inventor

Masakazu Taniguchi

Masatoshi Baba

Yoshinori Ochiai

Kiminori Hirata

Masayoshi Hirose

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.)

Nissan Chemical Corp

Original Assignee

Nissan Chemical Corp

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.)

1982-03-05

Filing date

1983-03-04

Publication date

1988-06-07

1982-03-05 Priority claimed from JP3499182A external-priority patent/JPS58152870A/ja

1982-08-27 Priority claimed from JP14944682A external-priority patent/JPS5939874A/ja

1982-10-18 Priority claimed from JP57182449A external-priority patent/JPS5970608A/ja

1982-11-25 Priority claimed from JP57206438A external-priority patent/JPH06760B2/ja

1983-03-04 Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp

1988-06-07 Application granted granted Critical

1988-06-07 Publication of CA1237721A publication Critical patent/CA1237721A/fr

Status Expired legal-status Critical Current

Links

230000000749 insecticidal effect Effects 0.000 title claims abstract description 18
230000000895 acaricidal effect Effects 0.000 title claims abstract description 13
230000000855 fungicidal effect Effects 0.000 title claims abstract description 12
230000001069 nematicidal effect Effects 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title abstract description 5
239000000203 mixture Substances 0.000 title description 25
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 109
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
239000001257 hydrogen Substances 0.000 claims abstract description 47
229910052736 halogen Inorganic materials 0.000 claims abstract description 33
150000002367 halogens Chemical class 0.000 claims abstract description 33
125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 16
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 8
229910007161 Si(CH3)3 Inorganic materials 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract 41
150000002431 hydrogen Chemical class 0.000 claims abstract 12
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
239000006096 absorbing agent Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
229940086542 triethylamine Drugs 0.000 claims 1
-1 5-substituted -3(2H)-pyridazinone Chemical class 0.000 abstract description 9
235000018936 Vitellaria paradoxa Nutrition 0.000 description 171
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 55
229920000180 alkyd Polymers 0.000 description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 18
239000000460 chlorine Substances 0.000 description 18
125000004435 hydrogen atom Chemical class [H]* 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
201000010099 disease Diseases 0.000 description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
240000008067 Cucumis sativus Species 0.000 description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
239000011737 fluorine Substances 0.000 description 10
229910052731 fluorine Inorganic materials 0.000 description 10
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
235000009849 Cucumis sativus Nutrition 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
239000004480 active ingredient Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 5
238000011081 inoculation Methods 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
241000500437 Plutella xylostella Species 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000000361 pesticidal effect Effects 0.000 description 4
239000011148 porous material Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000819999 Nymphes Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000004927 clay Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000000428 dust Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000005645 nematicide Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
OTOJGQWOSFQJAH-UHFFFAOYSA-N 4-hydroxy-1h-pyridazin-6-one Chemical class OC1=CC(=O)C=NN1 OTOJGQWOSFQJAH-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
235000009434 Actinidia chinensis Nutrition 0.000 description 2
244000298697 Actinidia deliciosa Species 0.000 description 2
235000009436 Actinidia deliciosa Nutrition 0.000 description 2
241000239290 Araneae Species 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
241000256059 Culex pipiens Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
241000243785 Meloidogyne javanica Species 0.000 description 2
241000257159 Musca domestica Species 0.000 description 2
241000358422 Nephotettix cincticeps Species 0.000 description 2
241000282320 Panthera leo Species 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
235000019504 cigarettes Nutrition 0.000 description 2
230000015271 coagulation Effects 0.000 description 2
238000005345 coagulation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000011630 iodine Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
230000024241 parasitism Effects 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000003236 psychic effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DNEPVPBJDHQGRK-UHFFFAOYSA-N 1-(chloromethyl)-4-cyclohexylbenzene Chemical compound C1=CC(CCl)=CC=C1C1CCCCC1 DNEPVPBJDHQGRK-UHFFFAOYSA-N 0.000 description 1
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
HLQZCRVEEQKNMS-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylbenzene Chemical group C1=CC(CCl)=CC=C1C1=CC=CC=C1 HLQZCRVEEQKNMS-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
HYHVRDPIPYBIRC-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-hydroxypyridazin-3-one Chemical compound CC(C)(C)N1N=CC(O)=C(Cl)C1=O HYHVRDPIPYBIRC-UHFFFAOYSA-N 0.000 description 1
PCECCKAMFLFMKU-UHFFFAOYSA-N 4-chloro-2-ethyl-5-[(4-trimethylsilylphenyl)methoxy]pyridazin-3-one Chemical compound O=C1N(CC)N=CC(OCC=2C=CC(=CC=2)[Si](C)(C)C)=C1Cl PCECCKAMFLFMKU-UHFFFAOYSA-N 0.000 description 1
QSMJDUYHPSVTBH-UHFFFAOYSA-N 4-chloro-2-ethyl-5-hydroxypyridazin-3-one Chemical compound CCN1N=CC(O)=C(Cl)C1=O QSMJDUYHPSVTBH-UHFFFAOYSA-N 0.000 description 1
LHWSOJJLYIMLKY-UHFFFAOYSA-N 4-chloro-5-hydroxy-2-propan-2-ylpyridazin-3-one Chemical compound CC(C)N1N=CC(O)=C(Cl)C1=O LHWSOJJLYIMLKY-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000255749 Coccinellidae Species 0.000 description 1
241000256054 Culex <genus> Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
241001299255 Henosepilachna Species 0.000 description 1
241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
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 1
241000124008 Mammalia Species 0.000 description 1
101100537948 Mus musculus Trir gene Proteins 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
239000008896 Opium Substances 0.000 description 1
241000233679 Peronosporaceae Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001281805 Pseudoperonospora cubensis Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
RYMLLIQMFOAKHX-UHFFFAOYSA-N [4-(bromomethyl)phenyl]-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=C(CBr)C=C1 RYMLLIQMFOAKHX-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
238000005065 mining Methods 0.000 description 1
230000003129 miticidal effect Effects 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
229960001027 opium Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000005461 organic phosphorous group Chemical group 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 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
238000002054 transplantation Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA000422912A 1982-03-05 1983-03-04 Derives de pyridazinone, leur preparation, et agents fongicides, insecticides, acaricides et nematocides pour l'horticulture et l'agriculture qui les renferment Expired CA1237721A (fr)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
JP34,991/1982		1982-03-05
JP3499182A JPS58152870A (ja)	1982-03-05	1982-03-05	ピリダジノン誘導体、その製法および該誘導体を有効成分とする農園芸用殺菌、殺虫、殺ダニ、殺センチユウ剤
JP14944682A JPS5939874A (ja)	1982-08-27	1982-08-27	ピリタジノン誘導体，その製造法および該誘導体を有効成分とする農園芸用殺菌，殺虫，殺ダニ，殺線虫剤
JP149,446/1982		1982-08-27
JP182,499/1982		1982-10-18
JP57182449A JPS5970608A (ja)	1982-10-18	1982-10-18	造形変化をする芳香剤
JP206,438/1982		1982-11-25
JP57206438A JPH06760B2 (ja)	1982-11-25	1982-11-25	ピリダジノン誘導体および農園芸用殺虫、殺ダニ、殺線虫剤

Publications (1)

Publication Number	Publication Date
CA1237721A true CA1237721A (fr)	1988-06-07

Family

ID=27460024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000422912A Expired CA1237721A (fr)	1982-03-05	1983-03-04	Derives de pyridazinone, leur preparation, et agents fongicides, insecticides, acaricides et nematocides pour l'horticulture et l'agriculture qui les renferment

Country Status (3)

Country	Link
AU (1)	AU563533B2 (fr)
BR (1)	BR8301107A (fr)
CA (1)	CA1237721A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3578304D1 (de) *	1984-11-29	1990-07-26	Nissan Chemical Ind Ltd	Pyridazinonderivate, deren herstellung und insektizidische, acaricidische, nematicidische, fungizidische zusammensetzungen.
US4837217A (en) *	1985-04-19	1989-06-06	Nissan Chemical Industries, Ltd.	Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions

1983
- 1983-03-04 AU AU12042/83A patent/AU563533B2/en not_active Ceased
- 1983-03-04 CA CA000422912A patent/CA1237721A/fr not_active Expired
- 1983-03-07 BR BR8301107A patent/BR8301107A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU563533B2 (en)	1987-07-16
BR8301107A (pt)	1983-11-22
AU1204283A (en)	1983-09-15

Legal Events

Date	Code	Title	Description
2005-06-07	MKEX	Expiry

Publication	Publication Date	Title
EP0134439B1 (fr)	1988-08-24	Dérivés de pyridazinone, leur préparation et compositions insecticides acaricides et fongicides
KR960012178B1 (ko)	1996-09-16	피리미딘 유도체, 그의 제조방법, 제초방법 및 제초조성물
EP0088384B1 (fr)	1986-12-30	Dérivés de pyridazinone, leur préparation et compositions fongicides, insecticides, acaricides, nématicides utilisées en agriculture et en horticulture contenant ces dérivés
EP0199281B1 (fr)	1991-07-10	Dérivés de pyridazinone, leur préparation et compositions insecticides, acaricides, nématicides, fongicides
EP0438209A1 (fr)	1991-07-24	Dérivés de l'uracil et pesticides contenant ces dérivés comme agent actif
EP0183212B1 (fr)	1990-06-20	Dérivés de pyridazinone, leur préparation et compositions insecticides, acaricides, nématicides et fongicides
EP0329020B1 (fr)	1991-01-30	Dérivés de pyrazole, procedés pour la préparation de ces composés, compositions insecticides, miticides et fongicides contenant ces dérivés comme ingrédients actifs
EP0232825B1 (fr)	1992-05-13	Dérivés de pyridazinone, leur préparation et compositions insecticides, acaricides, nématicides, fongicides
EP0339105A1 (fr)	1989-11-02	Composés hétérocycliques contenant de l'azote et compositions pour la lutte contre les parasites et/ou la prévention du mildiou
KR960012172B1 (ko)	1996-09-16	피라졸 유도체 및 이 유도체를 활성 성분으로 함유하는 살충제 및 살비제 조성물
EP0891975A1 (fr)	1999-01-20	Pyrazoles et produits chimiques a usage agricole contenant ces composes comme ingredients actifs
US4462994A (en)	1984-07-31	N-Containing heterocyclic ring-substituted O-arylphosphate derivatives, preparation thereof, and insecticides, acaricides and nematocides containing said derivatives
JP4838959B2 (ja)	2011-12-14	６−（１−フルオロエチル）−５−ヨード−４−アミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
JPH06762B2 (ja)	1994-01-05	ピリダジノン誘導体の製造法
KR100745205B1 (ko)	2007-08-02	6-(1-플루오로에틸)-5-요오도-4-아미노피리미딘 화합물, 그 제조 방법 및 농원예용 방제제
EP0476573B1 (fr)	1996-04-24	2-tButyl-4-chloro-5-(4-ibutylmethylcyclohexyl)-methylthio-3(H)-pyridazinone ayant une activité insecticide et acaricide
JPH07112972A (ja)	1995-05-02	ピラゾールカルボキサミド誘導体、その製法及び農園芸用の有害生物防除剤
EP0283271A2 (fr)	1988-09-21	Dérivés de pyridazinone, procédé pour leur production et insecticides, acaricides et fongicides contenant ces dérivés comme principe actif
JPH09278775A (ja)	1997-10-28	ピラゾール化合物及びこれを有効成分とする殺虫、殺ダニ、殺菌剤
US4327089A (en)	1982-04-27	O-(N-Alkoxy-pyridinecarboximidoyl) phosphates, process for producing the same, and insecticidal or acaridical compositions containing the same
JPH07118242A (ja)	1995-05-09	フェノキシアルキルアミン誘導体、その製法及び農園芸用の有害生物防除剤
US4210592A (en)	1980-07-01	Thiophosphoro-S-acylated hydrazones
JPH03153668A (ja)	1991-07-01	ピラゾールアミド類およびこれを有効成分とする殺虫、殺ダニ剤
JP2002234876A (ja)	2002-08-23	６−（１−フルオロエチル）−５−ヨード−４−アルキルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
JPH0826005B2 (ja)	1996-03-13	ピラゾール誘導体及びこれを有効成分とする殺虫、殺ダニ剤