CS212267B2 - Insekticidní, akaricidní a fungicidní prostředek a způsob výroby jeho účinné složky - Google Patents

Insekticidní, akaricidní a fungicidní prostředek a způsob výroby jeho účinné složky Download PDF

Info

Publication number: CS212267B2
Authority: CS; Czechoslovakia
Prior art keywords: parts; formula; active ingredient; mixture; isomers
Prior art date: 1977-02-11

Application number

CS88578A

Other languages

Czech (cs)

English (en)

Inventor

Jozef Drabek

Peter Ackermann

Saleem Farooq

Laurenz Gsell

Odd Kristiansen

Willy Meyer

Original Assignee

Ciba Geigy Ag

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.)

1977-02-11

Filing date

1978-02-10

Publication date

1982-03-26

1977-02-11 Priority claimed from CH169077A external-priority patent/CH625396A5/de

1977-07-28 Priority claimed from CH934777A external-priority patent/CH627921A5/de

1978-02-10 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1982-03-26 Publication of CS212267B2 publication Critical patent/CS212267B2/cs

Links

230000000895 acaricidal effect Effects 0.000 title claims description 7
230000000855 fungicidal effect Effects 0.000 title claims description 3
239000000642 acaricide Substances 0.000 title description 2
239000002917 insecticide Substances 0.000 title description 2
239000000417 fungicide Substances 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
239000000203 mixture Substances 0.000 claims description 34
239000000460 chlorine Substances 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 23
239000004480 active ingredient Substances 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 10
-1 cyclopropanecarboxylic acid ester Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000000654 additive Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
230000000749 insecticidal effect Effects 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000013543 active substance Substances 0.000 description 11
239000000243 solution Substances 0.000 description 7
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
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150000002191 fatty alcohols Chemical class 0.000 description 3
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PTWUJNIBSWMQFA-UHFFFAOYSA-N 3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C(Br)C(Cl)(Cl)Br)C1C(Cl)=O PTWUJNIBSWMQFA-UHFFFAOYSA-N 0.000 description 2
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239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
241000255777 Lepidoptera Species 0.000 description 2
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239000002202 Polyethylene glycol Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000256248 Spodoptera Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
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235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
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235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
CHLAOFANYRDCPD-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(Cl)=O CHLAOFANYRDCPD-UHFFFAOYSA-N 0.000 description 1
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BNARGNJKJAZKNK-UHFFFAOYSA-N CC#COP(O)=O Chemical class CC#COP(O)=O BNARGNJKJAZKNK-UHFFFAOYSA-N 0.000 description 1
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239000003513 alkali Substances 0.000 description 1
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150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
VRAIHTAYLFXSJJ-UHFFFAOYSA-N alumane Chemical compound [AlH3].[AlH3] VRAIHTAYLFXSJJ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
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244000038559 crop plants Species 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
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POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
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239000003995 emulsifying agent Substances 0.000 description 1
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230000002349 favourable effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000037406 food intake Effects 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
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150000004679 hydroxides Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
FHQKDLNFTINTBW-UHFFFAOYSA-N prop-1-ynyl carbamate Chemical class CC#COC(N)=O FHQKDLNFTINTBW-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

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

CS88578A 1977-02-11 1978-02-10 Insekticidní, akaricidní a fungicidní prostředek a způsob výroby jeho účinné složky CS212267B2 (cs)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH169077A CH625396A5 (en)	1977-02-11	1977-02-11	Pesticides
CH934777A CH627921A5 (en)	1977-07-28	1977-07-28	Pesticides

Publications (1)

Publication Number	Publication Date
CS212267B2 true CS212267B2 (cs)	1982-03-26

Family

ID=25688393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS88578A CS212267B2 (cs)	1977-02-11	1978-02-10	Insekticidní, akaricidní a fungicidní prostředek a způsob výroby jeho účinné složky

Country Status (4)

Country	Link
CS (1)	CS212267B2 (pl)
GR (1)	GR66116B (pl)
PL (1)	PL108415B1 (pl)
SU (1)	SU694048A3 (pl)

1978
- 1978-02-09 GR GR55410A patent/GR66116B/el unknown
- 1978-02-10 CS CS88578A patent/CS212267B2/cs unknown
- 1978-02-10 PL PL20455278A patent/PL108415B1/pl unknown
- 1978-02-10 SU SU782578491A patent/SU694048A3/ru active

Also Published As

Publication number	Publication date
PL204552A1 (pl)	1978-11-06
GR66116B (pl)	1981-01-16
PL108415B1 (en)	1980-04-30
SU694048A3 (ru)	1979-10-25

Publication	Publication Date	Title
US4172135A (en)	1979-10-23	Benzeneacetic acid ester derivatives
US4161536A (en)	1979-07-17	Pesticidal aliphatic carboxylates
US4161535A (en)	1979-07-17	Pesticidal 2-isopropyl-4-phenyl-3-butenoic acid benzyl esters
JPS6113459B2 (pl)	1986-04-14
GB1587352A (en)	1981-04-01	Cyclopropanecarboxylic acid esters
US4219564A (en)	1980-08-26	Vinylcyclopropanecarboxylic acid-3-phenoxy-α-vinylbenzyl esters, processes for producing them, and their use in combating pests
US4301304A (en)	1981-11-17	3-Phenoxy-α-(1',2'-dibromovinyl)-benxyl alcohol
GB1589955A (en)	1981-05-20	Cyclopropanecarboxylic acid esters
US4277494A (en)	1981-07-07	Novel esters
GB1588212A (en)	1981-04-15	Cyclopropanecarboxylic acid esters
CS212267B2 (cs)	1982-03-26	Insekticidní, akaricidní a fungicidní prostředek a způsob výroby jeho účinné složky
US4225616A (en)	1980-09-30	Tetrahaloethylcyclopropane-carboxylic acid esters
GB2058784A (en)	1981-04-15	Dihalovinylcyclopropanecarboxylic acid esters processes for producing them and their use in pest control and also -haloethynyl-3-phenoxy-benzyl alcohols
CA1152093A (en)	1983-08-16	Cyclopropane carboxylic acid esters
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CS208462B2 (cs)	1981-09-15	Insekticidní, akaricidní a fungicidní prostředek a způsob výroby účinné složky
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EP0010727B1 (de)	1984-01-18	Vinylcyclopropancarbonsäure-3-phenoxy-alpha-vinylbenzylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
CA1152094A (en)	1983-08-16	Cyclopropane carboxylic acid esters
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US4221812A (en)	1980-09-09	Pesticidal spiropentanecarboxylates
DE2805274A1 (de)	1978-08-17	Cyclopropankarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung
JPS6041662B2 (ja)	1985-09-18	シクロプロパンカンルボン酸エステル及びその製法並びに該化合物を有効成分とする殺虫、殺ダニ剤
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