CH636072A5 - Cyclopropanecarboxylates having a pesticidal action - Google Patents

Cyclopropanecarboxylates having a pesticidal action Download PDF

Info

Publication number: CH636072A5
Authority: CH; Switzerland
Prior art keywords: group; hydrogen atom; atom; formula; compounds according
Prior art date: 1977-03-31

Application number

CH335378A

Other languages

German (de)

English (en)

Inventor

John Hugh Davies

Michael John Bull

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.)

1977-03-31

Filing date

1978-03-29

Publication date

1983-05-13

1978-03-29 Application filed by Shell Int Research filed Critical Shell Int Research

1983-05-13 Publication of CH636072A5 publication Critical patent/CH636072A5/de

Links

YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims description 9
230000000361 pesticidal effect Effects 0.000 title claims description 4
-1 cyano, ethynyl Chemical group 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 31
239000003795 chemical substances by application Substances 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000000575 pesticide Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
125000000217 alkyl group Chemical group 0.000 claims 8
125000002947 alkylene group Chemical group 0.000 claims 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
125000005544 phthalimido group Chemical group 0.000 claims 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
229910052731 fluorine Chemical group 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
125000005059 halophenyl group Chemical group 0.000 claims 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
150000001447 alkali salts Chemical class 0.000 claims 1
150000001350 alkyl halides Chemical class 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
230000002349 favourable effect Effects 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910000027 potassium carbonate Inorganic materials 0.000 claims 1
125000001391 thioamide group Chemical group 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
241000255925 Diptera Species 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
241000257159 Musca domestica Species 0.000 description 5
230000000977 initiatory effect Effects 0.000 description 5
238000005507 spraying Methods 0.000 description 5
241000196324 Embryophyta Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241001124076 Aphididae Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241001608567 Phaedon cochleariae Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
241000256250 Spodoptera littoralis Species 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
230000006378 damage Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
241001425390 Aphis fabae Species 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241001608568 Phaedon Species 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
239000013504 Triton X-100 Substances 0.000 description 2
229920004890 Triton X-100 Polymers 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
210000001015 abdomen Anatomy 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
230000007797 corrosion Effects 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
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
BQDCBXQEHMGIDL-UHFFFAOYSA-N 1-[(5-benzylfuran-3-yl)methyl]-3-chloro-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C(C1(CC2=COC(=C2)CC3=CC=CC=C3)C(=O)O)Cl)C BQDCBXQEHMGIDL-UHFFFAOYSA-N 0.000 description 1
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
ZELGDKDDESZBPM-UHFFFAOYSA-N 3-chloro-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(Cl)C1C(Cl)=O ZELGDKDDESZBPM-UHFFFAOYSA-N 0.000 description 1
GHXJAGHRKSJMPQ-UHFFFAOYSA-N 3-chloro-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(Cl)C1C(O)=O GHXJAGHRKSJMPQ-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
235000016068 Berberis vulgaris Nutrition 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
241000254173 Coleoptera Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
240000000047 Gossypium barbadense Species 0.000 description 1
235000009429 Gossypium barbadense Nutrition 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
239000005909 Kieselgur Substances 0.000 description 1
241000257229 Musca <genus> Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 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
229930006000 Sucrose Natural products 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 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
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000012184 mineral wax Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002245 particle Substances 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
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 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
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
238000010998 test method Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 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
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D209/49—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Indole Compounds (AREA)
Furan Compounds (AREA)

CH335378A 1977-03-31 1978-03-29 Cyclopropanecarboxylates having a pesticidal action CH636072A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB13621/77A GB1597487A (en)	1977-03-31	1977-03-31	Pesticidal cyclopropane carboxylates

Publications (1)

Publication Number	Publication Date
CH636072A5 true CH636072A5 (en)	1983-05-13

Family

ID=10026377

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH335378A CH636072A5 (en)	1977-03-31	1978-03-29	Cyclopropanecarboxylates having a pesticidal action

Country Status (17)

Country	Link
JP (1)	JPS53121744A (it)
AU (1)	AU515078B2 (it)
BE (1)	BE865430A (it)
BR (1)	BR7801928A (it)
CA (1)	CA1093563A (it)
CH (1)	CH636072A5 (it)
DE (1)	DE2813552A1 (it)
DK (1)	DK139378A (it)
EG (1)	EG13297A (it)
ES (1)	ES468309A1 (it)
FR (1)	FR2385678A1 (it)
GB (1)	GB1597487A (it)
IL (1)	IL54381A (it)
IT (1)	IT1096165B (it)
NL (1)	NL7803355A (it)
SE (1)	SE427553B (it)
ZA (1)	ZA781796B (it)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1437789A (en) *	1973-02-16	1976-06-03	Shell Int Research	Cyclopropane derivatives and their use as pesticides
US3973035A (en) *	1973-05-15	1976-08-03	Shell Oil Company	Cyanobenzyl cyclopropane carboxylate pesticides
GB1533854A (en) *	1975-03-11	1978-11-29	Shell Int Research	Benzyl thioamides and their use as pesticides

1977
- 1977-03-31 GB GB13621/77A patent/GB1597487A/en not_active Expired
1978
- 1978-02-24 CA CA297,703A patent/CA1093563A/en not_active Expired
- 1978-03-25 EG EG199/78A patent/EG13297A/xx active
- 1978-03-29 AU AU34534/78A patent/AU515078B2/en not_active Expired
- 1978-03-29 FR FR7809056A patent/FR2385678A1/fr active Granted
- 1978-03-29 ZA ZA00781796A patent/ZA781796B/xx unknown
- 1978-03-29 BR BR7801928A patent/BR7801928A/pt unknown
- 1978-03-29 IL IL54381A patent/IL54381A/xx unknown
- 1978-03-29 DK DK139378A patent/DK139378A/da not_active IP Right Cessation
- 1978-03-29 DE DE19782813552 patent/DE2813552A1/de not_active Withdrawn
- 1978-03-29 SE SE7803561A patent/SE427553B/sv unknown
- 1978-03-29 ES ES468309A patent/ES468309A1/es not_active Expired
- 1978-03-29 CH CH335378A patent/CH636072A5/de not_active IP Right Cessation
- 1978-03-29 JP JP3539778A patent/JPS53121744A/ja active Pending
- 1978-03-29 BE BE186362A patent/BE865430A/xx not_active IP Right Cessation
- 1978-03-29 IT IT7821740A patent/IT1096165B/it active
- 1978-03-30 NL NL7803355A patent/NL7803355A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA781796B (en)	1979-03-28
NL7803355A (nl)	1978-10-03
SE427553B (sv)	1983-04-18
GB1597487A (en)	1981-09-09
BR7801928A (pt)	1978-12-19
CA1093563A (en)	1981-01-13
FR2385678B1 (it)	1980-12-26
IL54381A0 (en)	1978-06-15
AU3453478A (en)	1979-10-04
IT7821740A0 (it)	1978-03-29
IL54381A (en)	1981-05-20
FR2385678A1 (fr)	1978-10-27
DE2813552A1 (de)	1978-10-05
DK139378A (da)	1978-10-01
IT1096165B (it)	1985-08-17
AU515078B2 (en)	1981-03-12
BE865430A (fr)	1978-09-29
ES468309A1 (es)	1979-09-16
EG13297A (en)	1981-03-31
SE7803561L (sv)	1978-10-01
JPS53121744A (en)	1978-10-24

Legal Events

Date	Code	Title	Description
1985-11-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH630778A5 (de)	1982-07-15	Schaedlingsbekaempfungsmittel enthaltend einen substituierten benzylaether oder -thioaether.
DE2407024A1 (de)	1974-08-29	Zur schaedlingsbekaempfung geeignete cyclopropanderivate und verfahren zu ihrer herstellung
CH624831A5 (it)	1981-08-31
DE2603877C2 (de)	1985-03-07	Oxadiazolinonverbindungen, ihre Herstellung und sie enthaltendes Mittel
EP0129513A2 (de)	1984-12-27	Oxamidsäure-Derivate
EP0300968B1 (de)	1991-12-11	N-Benzoyl-N'-2,5-dihalogen-4-perfluoro-alkoxyphenylharnstoffe, ihre Herstellung und Verwendung bei der Kontrolle von Schädlingen
DE1667979C3 (de)	1978-06-01	13-Benzodioxolcarbamate sowie Verfahren zu deren Herstellung und Schädlingsbekämpfungsmittel mit einem Gehalt dieser Verbindungen
DE2422977C2 (de)	1984-01-12	Cyclopropan-carbonsäure-&alpha;-cyanbenzylester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pestizide Mittel
DE1137259B (de)	1962-09-27	Selektive Bekaempfung von Fingerhirse
EP0055213B1 (de)	1986-02-26	Phenylharnstoffe
CH639532A5 (de)	1983-11-30	Insektizide carbonsaeureester von alpha-trifluormethyl-3-phenoxybenzylalkohol.
DE2941332C2 (it)	1988-10-06
CH616311A5 (it)	1980-03-31
EP0098800A1 (de)	1984-01-18	Carbaminsäureester
CH632241A5 (en)	1982-09-30	Benzyl oxime ethers with pesticidal activity
DD215002A5 (de)	1984-10-31	Pestizide zusammensetzung
CH636072A5 (en)	1983-05-13	Cyclopropanecarboxylates having a pesticidal action
DE2061133A1 (de)	1971-06-24	Pestizide Verbindung,Verfahren zu ihrer Herstellung und Verwendung
EP0136451A2 (de)	1985-04-10	Arylmethylätherderivate, Schädlingsbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung
DE2941312C2 (it)	1989-01-26
EP0327504B1 (de)	1993-05-12	N-Benzoyl-N'-trifluorphenylharnstoffe, ihre Herstellung und Verwendung bei der Kontrolle von Schädlingen
CH629082A5 (de)	1982-04-15	Schaedlingsbekaempfungsmittel enthaltend neue dispirocyclopropancarbonsaeureester als wirkstoffkomponente.
DD236868A5 (de)	1986-06-25	Mittel zum protahieren der wirkungsdauer und zur erhoehung der selektivitaet von herbiziden zusammensetzungen
EP0101662A2 (de)	1984-02-29	Benzoylparabansäuren
DE3832656A1 (de)	1989-04-13	Substituierte carbamate