CH632241A5 - Benzyl oxime ethers with pesticidal activity - Google Patents

Benzyl oxime ethers with pesticidal activity Download PDF

Info

Publication number: CH632241A5
Authority: CH; Switzerland
Prior art keywords: group; carbon atoms; compounds according; formula; ketoxime
Prior art date: 1977-02-18

Application number

CH171078A

Other languages

German (de)

English (en)

Inventor

Michael John Bull

Robert John Griffith Searle

Original Assignee

Shell Int Research

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.)

1977-02-18

Filing date

1978-02-16

Publication date

1982-09-30

1978-02-16 Application filed by Shell Int Research filed Critical Shell Int Research

1982-09-30 Publication of CH632241A5 publication Critical patent/CH632241A5/de

Links

-1 Benzyl oxime ethers Chemical class 0.000 title claims description 32
230000000361 pesticidal effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
150000001447 alkali salts Chemical class 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
241000607479 Yersinia pestis Species 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000000262 haloalkenyl group Chemical group 0.000 claims description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
125000004212 difluorophenyl group Chemical group 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241000255967 Helicoverpa zea Species 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 4
241000238876 Acari Species 0.000 description 4
241000255925 Diptera Species 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
241000256250 Spodoptera littoralis Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000575 pesticide Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241000238631 Hexapoda Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000257159 Musca domestica Species 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
241000238680 Rhipicephalus microplus Species 0.000 description 3
239000000654 additive Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000035515 penetration Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000007865 diluting Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229910052701 rubidium Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
239000012085 test solution Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
XCOKKVWDJYSCRZ-UHFFFAOYSA-N 1-phenoxy-3-[(3-phenoxyphenyl)methoxymethyl]benzene Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1COCC(C=1)=CC=CC=1OC1=CC=CC=C1 XCOKKVWDJYSCRZ-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
240000001624 Espostoa lanata Species 0.000 description 1
235000009161 Espostoa lanata Nutrition 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
FBEOOKIEVDOCBA-UHFFFAOYSA-N N-[bis(2-cyclobutyl-4-fluorophenyl)methylidene]hydroxylamine Chemical compound C1(CCC1)C1=C(C=CC(=C1)F)C(=NO)C1=C(C=C(C=C1)F)C1CCC1 FBEOOKIEVDOCBA-UHFFFAOYSA-N 0.000 description 1
XXIAZPFRZXLMJN-UHFFFAOYSA-N N-[bis(2-cyclopropyl-4-fluorophenyl)methylidene]hydroxylamine Chemical compound C1(CC1)C1=C(C=CC(=C1)F)C(=NO)C1=C(C=C(C=C1)F)C1CC1 XXIAZPFRZXLMJN-UHFFFAOYSA-N 0.000 description 1
QLNORYPJYNLPQZ-UHFFFAOYSA-N N-[bis(4-chloro-2-cyclopropylphenyl)methylidene]hydroxylamine Chemical compound C1(CC1)C1=C(C=CC(=C1)Cl)C(=NO)C1=C(C=C(C=C1)Cl)C1CC1 QLNORYPJYNLPQZ-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
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238000010171 animal model Methods 0.000 description 1
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OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical class [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
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125000001309 chloro group Chemical group Cl* 0.000 description 1
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
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239000003112 inhibitor Substances 0.000 description 1
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230000016507 interphase Effects 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
229910052622 kaolinite Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
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239000010445 mica Substances 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
PQNLRWKQNYBVJS-UHFFFAOYSA-N n-[cyclopropyl-(2,4-dimethylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(C)=CC=C1C(=NO)C1CC1 PQNLRWKQNYBVJS-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
238000010998 test method Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH171078A 1977-02-18 1978-02-16 Benzyl oxime ethers with pesticidal activity CH632241A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7012/77A GB1594261A (en)	1977-02-18	1977-02-18	Benzyloxime ethers

Publications (1)

Publication Number	Publication Date
CH632241A5 true CH632241A5 (en)	1982-09-30

Family

ID=9824960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH171078A CH632241A5 (en)	1977-02-18	1978-02-16	Benzyl oxime ethers with pesticidal activity

Country Status (19)

Country	Link
JP (1)	JPS53103449A (da)
AU (1)	AU517746B2 (da)
BE (1)	BE863890A (da)
BR (1)	BR7800948A (da)
CA (1)	CA1166652A (da)
CH (1)	CH632241A5 (da)
DE (1)	DE2806664A1 (da)
DK (1)	DK69878A (da)
ES (1)	ES467027A1 (da)
FR (1)	FR2381025A1 (da)
GB (1)	GB1594261A (da)
IE (1)	IE46335B1 (da)
IL (1)	IL54061A (da)
IT (1)	IT7820345A0 (da)
LU (1)	LU79074A1 (da)
MX (1)	MX5186E (da)
NL (1)	NL7801734A (da)
TR (1)	TR19839A (da)
ZA (1)	ZA78914B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4158015A (en) *	1978-08-16	1979-06-12	Mobil Oil Corporation	Process for the stereoselective synthesis of the E isomer of aryl alkyl oximes
US4269330A (en) *	1979-10-11	1981-05-26	Johnson Terry J	Cartridge type sauce extruder
JPS58150559A (ja) *	1982-03-04	1983-09-07	Sumitomo Chem Co Ltd	オキシムエ−テル誘導体、その製造法およびそれを有効成分として含有する殺虫剤
IL75858A (en) *	1984-07-31	1989-02-28	Commw Scient Ind Res Org	Substituted benzyl ethers of oximes,their production and their use as arthropodicides
DE4213149A1 (de) *	1992-04-22	1993-10-28	Hoechst Ag	Akarizide, insektizide und nematizide substituierte (Hetero)-Aryl-Alkyl-ketonoxim-O-ether, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel
CN1177824C (zh)	2000-06-15	2004-12-01	大正制药株式会社	羟基甲脒衍生物及含有该衍生物的药物

1977
- 1977-02-18 GB GB7012/77A patent/GB1594261A/en not_active Expired
1978
- 1978-01-11 CA CA000294719A patent/CA1166652A/en not_active Expired
- 1978-02-13 BE BE1008708A patent/BE863890A/xx not_active IP Right Cessation
- 1978-02-16 ES ES467027A patent/ES467027A1/es not_active Expired
- 1978-02-16 TR TR19839A patent/TR19839A/xx unknown
- 1978-02-16 LU LU79074A patent/LU79074A1/xx unknown
- 1978-02-16 JP JP1600278A patent/JPS53103449A/ja active Pending
- 1978-02-16 BR BR7800948A patent/BR7800948A/pt unknown
- 1978-02-16 IT IT7820345A patent/IT7820345A0/it unknown
- 1978-02-16 IE IE334/78A patent/IE46335B1/en unknown
- 1978-02-16 DK DK69878A patent/DK69878A/da not_active Application Discontinuation
- 1978-02-16 MX MX786865U patent/MX5186E/es unknown
- 1978-02-16 AU AU33347/78A patent/AU517746B2/en not_active Expired
- 1978-02-16 IL IL54061A patent/IL54061A/xx unknown
- 1978-02-16 FR FR7804390A patent/FR2381025A1/fr active Granted
- 1978-02-16 ZA ZA00780914A patent/ZA78914B/xx unknown
- 1978-02-16 DE DE19782806664 patent/DE2806664A1/de not_active Withdrawn
- 1978-02-16 CH CH171078A patent/CH632241A5/de not_active IP Right Cessation
- 1978-02-16 NL NL7801734A patent/NL7801734A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
GB1594261A (en)	1981-07-30
TR19839A (tr)	1980-01-28
DK69878A (da)	1978-08-19
IL54061A (en)	1982-05-31
AU3334778A (en)	1979-08-23
IL54061A0 (en)	1978-04-30
JPS53103449A (en)	1978-09-08
IE46335B1 (en)	1983-05-04
FR2381025A1 (fr)	1978-09-15
ES467027A1 (es)	1978-10-16
DE2806664A1 (de)	1978-08-24
NL7801734A (nl)	1978-08-22
ZA78914B (en)	1979-01-31
MX5186E (es)	1983-04-21
IT7820345A0 (it)	1978-02-16
FR2381025B1 (da)	1980-04-04
IE780334L (en)	1978-08-18
BR7800948A (pt)	1978-11-28
CA1166652A (en)	1984-05-01
AU517746B2 (en)	1981-08-27
BE863890A (nl)	1978-08-14
LU79074A1 (fr)	1978-09-28

Legal Events

Date	Code	Title	Description
1985-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2822304A1 (de)	1978-11-30	Substituierte cyclohexan-1,3-dion- derivate
CH630778A5 (de)	1982-07-15	Schaedlingsbekaempfungsmittel enthaltend einen substituierten benzylaether oder -thioaether.
EP0001203A1 (de)	1979-04-04	N-Phenyl-N'-Benzoylharnstoffe, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und ihre Verwendung in der Schädlingsbekämpfung
EP0129513B1 (de)	1988-05-18	Oxamidsäure-Derivate
CH648294A5 (de)	1985-03-15	Cyclohexan-1,3-dion-derivate, verfahren zu ihrer herstellung und sie enthaltende herbizide.
EP0175649A2 (de)	1986-03-26	Substituierte Carbodiimide
CH632241A5 (en)	1982-09-30	Benzyl oxime ethers with pesticidal activity
EP0055213B1 (de)	1986-02-26	Phenylharnstoffe
DE2706184A1 (de)	1977-08-18	Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
EP0179020A2 (de)	1986-04-23	Thioxanthene in der Schädlingsbekämpfung
DD210190A5 (de)	1984-06-06	Herbizides mittel
EP0198791A1 (de)	1986-10-22	Difluorcyclopropanderivate, Verfahren zu ihrer Herstellung sowie Schädlingsbekämpfungsmittel enthaltend diese Verbindungen
DE2744385A1 (de)	1978-04-06	Arylhydrazonderivate, verfahren zu ihrer herstellung und biocide mittel, enthaltend diese verbindungen
DE2524578A1 (de)	1975-12-11	Barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DE2919816C2 (da)	1987-10-22
EP0136451A2 (de)	1985-04-10	Arylmethylätherderivate, Schädlingsbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung
DE1542952A1 (de)	1970-07-16	Insekticides Wirkstoffgemisch und Verfahren zur Herstellung von Verbindungen mit insekticider Wirkung
EP0145662A2 (de)	1985-06-19	Isothioharnstoffe
DE2642850A1 (de)	1977-04-07	2,2-dimethyl-4,5-benzospiro(2,4)heptan- und 2,2-dimethyl-4,5-benzospiro (2,4)hepta-4,6-dien-1-carbonsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
DE2926408A1 (de)	1980-01-17	Benzyloxim-aether-derivate
DE2013955A1 (de)	1970-10-08	Insektizides und fungizides Mittel zur Verwendung in Landwirtschaft und Gartenbau
EP0059686A1 (de)	1982-09-08	Cyclopropankarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung
DE2548450A1 (de)	1976-05-13	Schaedlingsbekaempfungsmittel
CH629082A5 (de)	1982-04-15	Schaedlingsbekaempfungsmittel enthaltend neue dispirocyclopropancarbonsaeureester als wirkstoffkomponente.
EP0035971A2 (de)	1981-09-16	Oximphosphate, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung