SK5992002A3 - Oxime O-ether compounds and fungicides for agricultural and horticultural use - Google Patents

Oxime O-ether compounds and fungicides for agricultural and horticultural use Download PDF

Info

Publication number: SK5992002A3
Authority: SK; Slovakia
Prior art keywords: ome; alkyl; mmol; oxime; mixture
Prior art date: 1999-11-05

Application number

SK599-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Hiroshi Sano

Tadashi Sugiura

Yuuki Nakagawa

Hiroshi Hamamura

Akira Mitani

Takahiro Ando

Original Assignee

Nippon Soda Co

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.)

1999-11-05

Filing date

2000-11-02

Publication date

2003-02-04

2000-11-02 Application filed by Nippon Soda Co filed Critical Nippon Soda Co

2003-02-04 Publication of SK5992002A3 publication Critical patent/SK5992002A3/sk

Links

239000000417 fungicide Substances 0.000 title claims abstract description 42
150000002923 oximes Chemical class 0.000 title abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 106
230000000855 fungicidal effect Effects 0.000 claims abstract description 18
239000004480 active ingredient Substances 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
-1 cyano, nitro, amino Chemical group 0.000 claims description 78
125000000217 alkyl group Chemical group 0.000 claims description 24
238000003898 horticulture Methods 0.000 claims description 8
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims 2
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 151
239000000203 mixture Substances 0.000 description 98
239000000243 solution Substances 0.000 description 95
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
238000006243 chemical reaction Methods 0.000 description 56
125000001309 chloro group Chemical group Cl* 0.000 description 47
239000012043 crude product Substances 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
239000010410 layer Substances 0.000 description 32
238000002360 preparation method Methods 0.000 description 30
238000009472 formulation Methods 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
241000196324 Embryophyta Species 0.000 description 23
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
241001465180 Botrytis Species 0.000 description 17
238000001816 cooling Methods 0.000 description 17
238000010898 silica gel chromatography Methods 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000005457 ice water Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000003480 eluent Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 10
241000123650 Botrytis cinerea Species 0.000 description 10
241000221785 Erysiphales Species 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
239000003921 oil Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000001914 filtration Methods 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000000843 powder Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
235000011430 Malus pumila Nutrition 0.000 description 8
244000070406 Malus silvestris Species 0.000 description 8
235000015103 Malus silvestris Nutrition 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
125000001246 bromo group Chemical group Br* 0.000 description 8
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 8
241000233866 Fungi Species 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
206010039509 Scab Diseases 0.000 description 7
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
WORNMIRYYMSPOY-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1CCl WORNMIRYYMSPOY-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
244000046052 Phaseolus vulgaris Species 0.000 description 6
229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
239000002917 insecticide Substances 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
230000000895 acaricidal effect Effects 0.000 description 5
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 5
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
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 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
240000007049 Juglans regia Species 0.000 description 4
235000009496 Juglans regia Nutrition 0.000 description 4
PVJXCEWZXTURAF-UHFFFAOYSA-N N-[1-(4,6-dimethylpyridin-2-yl)ethylidene]hydroxylamine Chemical compound ON=C(C)C1=CC(C)=CC(C)=N1 PVJXCEWZXTURAF-UHFFFAOYSA-N 0.000 description 4
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 4
239000000642 acaricide Substances 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
244000038559 crop plants Species 0.000 description 4
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 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
238000000605 extraction Methods 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
239000004546 suspension concentrate Substances 0.000 description 4
235000020234 walnut Nutrition 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 3
WULXGCDMVLQZBT-UHFFFAOYSA-N 4-iodo-1-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(I)C=C1[N+]([O-])=O WULXGCDMVLQZBT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
231100000674 Phytotoxicity Toxicity 0.000 description 3
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
241000228452 Venturia inaequalis Species 0.000 description 3
239000002585 base Substances 0.000 description 3
125000005997 bromomethyl group Chemical group 0.000 description 3
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
239000004927 clay Substances 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
230000001804 emulsifying effect Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
239000010419 fine particle Substances 0.000 description 3
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 3
IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000012669 liquid formulation Substances 0.000 description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
239000000047 product Substances 0.000 description 3
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
XNIABQWETIDWCR-UHFFFAOYSA-N (4-chloro-6-methylpyridin-2-yl)methanol Chemical compound CC1=CC(Cl)=CC(CO)=N1 XNIABQWETIDWCR-UHFFFAOYSA-N 0.000 description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 2
LFDMJAPCFNGVAN-UHFFFAOYSA-N 1-(4-chloro-6-methylpyridin-2-yl)-n-[(2,6-dimethoxyphenyl)methoxy]ethanimine Chemical compound COC1=CC=CC(OC)=C1CON=C(C)C1=CC(Cl)=CC(C)=N1 LFDMJAPCFNGVAN-UHFFFAOYSA-N 0.000 description 2
NLXINSLPJMHYKN-UHFFFAOYSA-N 1-(4-chloro-6-methylpyridin-2-yl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC(C)=N1 NLXINSLPJMHYKN-UHFFFAOYSA-N 0.000 description 2
BQBRGOQCWAXXLR-UHFFFAOYSA-N 1-(chloromethyl)-2,4-dimethoxybenzene Chemical compound COC1=CC=C(CCl)C(OC)=C1 BQBRGOQCWAXXLR-UHFFFAOYSA-N 0.000 description 2
RRLMRRBVFFQATR-UHFFFAOYSA-N 1-(chloromethyl)-3-methoxy-2-(methoxymethoxy)benzene Chemical compound COCOC1=C(CCl)C=CC=C1OC RRLMRRBVFFQATR-UHFFFAOYSA-N 0.000 description 2
MEJFSMMBMUHMAU-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1CBr MEJFSMMBMUHMAU-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 2
RSUXBVFWXWSQER-UHFFFAOYSA-N 2-(bromomethyl)-1-methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1CBr RSUXBVFWXWSQER-UHFFFAOYSA-N 0.000 description 2
QWZQICKUZAGVFN-UHFFFAOYSA-N 2-(bromomethyl)-1-methoxy-3-nitrobenzene Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CBr QWZQICKUZAGVFN-UHFFFAOYSA-N 0.000 description 2
JJCHKLPYNULYDQ-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-3-methoxybenzene Chemical compound COC1=CC=CC(F)=C1CCl JJCHKLPYNULYDQ-UHFFFAOYSA-N 0.000 description 2
NOMLCULZXAQJQC-UHFFFAOYSA-N 2-[(2,4,6-trimethoxyphenyl)methoxy]isoindole-1,3-dione Chemical compound COC1=CC(OC)=CC(OC)=C1CON1C(=O)C2=CC=CC=C2C1=O NOMLCULZXAQJQC-UHFFFAOYSA-N 0.000 description 2
GTXTWVPORPPCJZ-UHFFFAOYSA-N 2-[[1-(4,6-dimethylpyridin-2-yl)ethylideneamino]oxymethyl]-6-methoxyphenol Chemical compound COC1=CC=CC(CON=C(C)C=2N=C(C)C=C(C)C=2)=C1O GTXTWVPORPPCJZ-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 2
VLNYLEMSSXHBPF-UHFFFAOYSA-N 4-chloro-6-methylpyridine-2-carbonitrile Chemical compound CC1=CC(Cl)=CC(C#N)=N1 VLNYLEMSSXHBPF-UHFFFAOYSA-N 0.000 description 2
244000291564 Allium cepa Species 0.000 description 2
235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
241000530549 Cercospora beticola Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
235000009849 Cucumis sativus Nutrition 0.000 description 2
239000005896 Etofenprox Substances 0.000 description 2
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235000010469 Glycine max Nutrition 0.000 description 2
241000896246 Golovinomyces cichoracearum Species 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
239000005867 Iprodione Substances 0.000 description 2
244000081841 Malus domestica Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
FZLBAJDREAOFPD-UHFFFAOYSA-N N-[1-(4-chloro-6-methylpyridin-2-yl)ethylidene]hydroxylamine Chemical compound ON=C(C)C1=CC(Cl)=CC(C)=N1 FZLBAJDREAOFPD-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
241000221662 Sclerotinia Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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229910052740 iodine Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
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 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
239000010721 machine oil Substances 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
229920000940 maneb Polymers 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
JTXXVKVAPICXLW-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methoxy]-1-(4,6-dimethylpyridin-2-yl)ethanimine Chemical compound COC1=CC(OC)=CC=C1CON=C(C)C1=CC(C)=CC(C)=N1 JTXXVKVAPICXLW-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
VFMNFJOSIWGNPD-UHFFFAOYSA-N o-[(2,4,6-trimethoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC(OC)=C(CON)C(OC)=C1 VFMNFJOSIWGNPD-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
235000021017 pears Nutrition 0.000 description 1
OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
239000010773 plant oil Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
238000007867 post-reaction treatment Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229940080817 rotenone Drugs 0.000 description 1
JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
229960005199 tetramethrin Drugs 0.000 description 1
239000004308 thiabendazole Substances 0.000 description 1
235000010296 thiabendazole Nutrition 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
229960004546 thiabendazole Drugs 0.000 description 1
DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

SK599-2002A 1999-11-05 2000-11-02 Oxime O-ether compounds and fungicides for agricultural and horticultural use SK5992002A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP31454499		1999-11-05
JP2000096516		2000-03-31
PCT/JP2000/007744 WO2001034568A1 (en)	1999-11-05	2000-11-02	Oxime o-ether compounds and fungicides for agricultural and horticultural use

Publications (1)

Publication Number	Publication Date
SK5992002A3 true SK5992002A3 (en)	2003-02-04

Family

ID=26567980

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK599-2002A SK5992002A3 (en)	1999-11-05	2000-11-02	Oxime O-ether compounds and fungicides for agricultural and horticultural use

Country Status (25)

Country	Link
US (1)	US6589967B1 (de)
EP (1)	EP1236717B1 (de)
JP (1)	JP4726373B2 (de)
KR (1)	KR100447464B1 (de)
CN (1)	CN1172916C (de)
AT (1)	ATE258753T1 (de)
AU (1)	AU756980B2 (de)
BG (1)	BG106654A (de)
BR (1)	BR0015318A (de)
CA (1)	CA2389805A1 (de)
DE (1)	DE60008142T2 (de)
DK (1)	DK1236717T3 (de)
EA (1)	EA004574B1 (de)
ES (1)	ES2211634T3 (de)
HK (1)	HK1052344A1 (de)
HU (1)	HUP0203849A3 (de)
IL (1)	IL149213A0 (de)
MX (1)	MXPA02004452A (de)
NZ (1)	NZ518452A (de)
PL (1)	PL361304A1 (de)
PT (1)	PT1236717E (de)
SK (1)	SK5992002A3 (de)
TR (2)	TR200301650T4 (de)
WO (1)	WO2001034568A1 (de)
YU (1)	YU33202A (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPWO2002064566A1 (ja) *	2001-02-14	2004-06-10	日本曹達株式会社	オキシムｏ−エーテル化合物及び農園芸用殺菌剤
US20040116480A1 (en) *	2001-02-20	2004-06-17	Yuki Nakagawa	Oxime ether compound and agricultural or horticultural bactericide
WO2003006432A1 (en) *	2001-07-09	2003-01-23	Nippon Soda Co.,Ltd.	Oxime ether compound and agricultural or horticultural bactericide
TW200306154A (en) *	2002-04-15	2003-11-16	Nippon Soda Co	Novel oxime O-ether compound, production process, and agricultural or horticultural bactericide
TW200307669A (en) *	2002-04-15	2003-12-16	Nippon Soda Co	Novel oxime o-ether compound, production process thereof, and agricultural or horticultural bactericide
CN100579956C (zh) *	2003-12-12	2010-01-13	湖南化工研究院	杀虫、杀菌的含硫、氧肟醚类化合物
ZA200901553B (en) *	2006-09-12	2010-06-30	Nippon Soda Co	Pest control agent in form of stable suspension
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2000
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- 2000-11-02 PL PL36130400A patent/PL361304A1/xx unknown
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- 2000-11-02 EP EP00971763A patent/EP1236717B1/de not_active Expired - Lifetime
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- 2000-11-02 CA CA002389805A patent/CA2389805A1/en not_active Abandoned
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- 2000-11-02 DK DK00971763T patent/DK1236717T3/da active
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Also Published As

Publication number	Publication date
HUP0203849A3 (en)	2003-04-28
PT1236717E (pt)	2004-06-30
ES2211634T3 (es)	2004-07-16
BG106654A (en)	2003-01-31
BR0015318A (pt)	2002-10-08
KR20020059686A (ko)	2002-07-13
EP1236717A4 (de)	2003-01-02
US6589967B1 (en)	2003-07-08
AU756980B2 (en)	2003-01-30
TR200301650T4 (tr)	2004-03-22
JP4726373B2 (ja)	2011-07-20
EA004574B1 (ru)	2004-06-24
HK1052344A1 (zh)	2003-09-11
CN1172916C (zh)	2004-10-27
YU33202A (sh)	2004-12-31
KR100447464B1 (ko)	2004-09-07
NZ518452A (en)	2004-05-28
DE60008142T2 (de)	2004-07-08
ATE258753T1 (de)	2004-02-15
DK1236717T3 (da)	2004-06-07
WO2001034568A1 (en)	2001-05-17
HUP0203849A2 (hu)	2003-03-28
EP1236717B1 (de)	2004-02-04
IL149213A0 (en)	2002-11-10
PL361304A1 (en)	2004-10-04
EA200200537A1 (ru)	2002-10-31
MXPA02004452A (es)	2002-10-23
TR200201223T2 (tr)	2002-09-23
CN1387515A (zh)	2002-12-25
AU1055301A (en)	2001-06-06
DE60008142D1 (de)	2004-03-11
CA2389805A1 (en)	2001-05-17
EP1236717A1 (de)	2002-09-04

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