IL27735A - Oximecarbamates,their preparation and their use as insecticides and acaricides - Google Patents
Oximecarbamates,their preparation and their use as insecticides and acaricidesInfo
- Publication number
- IL27735A IL27735A IL27735A IL2773567A IL27735A IL 27735 A IL27735 A IL 27735A IL 27735 A IL27735 A IL 27735A IL 2773567 A IL2773567 A IL 2773567A IL 27735 A IL27735 A IL 27735A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- active
- active compound
- weight
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 16
- 230000000895 acaricidal effect Effects 0.000 title description 4
- 239000000642 acaricide Substances 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 50
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000006378 damage Effects 0.000 description 11
- -1 benain Chemical class 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 241000238876 Acari Species 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 6
- 241000255925 Diptera Species 0.000 description 5
- 241001454295 Tetranychidae Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 241001124076 Aphididae Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000238818 Acheta domesticus Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 235000011303 Brassica alboglabra Nutrition 0.000 description 2
- 235000011302 Brassica oleracea Nutrition 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000500439 Plutella Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000255580 Ceratitis <genus> Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001659689 Hercinothrips Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000347881 Kadua laxiflora Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- 241001599018 Melanogaster Species 0.000 description 1
- 241000254071 Melolontha Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000721623 Myzus Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- WSOLOEJZQRGZNK-UHFFFAOYSA-N N-(2-dodecylsulfanylethylidene)hydroxylamine Chemical compound C(CCCCCCCCCCC)SCC=NO WSOLOEJZQRGZNK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- 241000125162 Rhopalosiphum Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 231100000018 phototoxicity Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000003738 xylenes Chemical class 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- 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)
Description
27735/2 Λτ+ρ ΉκρκΛ θ' ηπ '^υι Tina οπη Oximecarbamates, their preparation and their uae as insecticidea and acaricidea FARBENPABRIKEN BAYER AKTIENGESELL CflAFT C. 26282 The present Invention relates to new oximecarbamates• which have insecticidal and acaricidal properties, and to processes for their preparation* It is known to use carbamates aa ineecticidal and acaricidal active compounds. Thus* 3-eethyl-4-dimethyl-attinophenyl-N-methylcarbaaate (see U.S. Patent Specifica ion 3»t34,806), B-naphthyl-HHDethylcarbaiJ-ate (see U,3. Patent Specification 2,903,478) and ieopropylmeth lpyrazolyl-K,N-dimethylcarbaaate (see Swiss Patent Specification 282,655) play a considerable part in practice.
The new oximecarbamates according to the invention have the formula C in which R is an alkyl or phenyl radical, ia a lo¾er alkyl radical, and Eg la hydrogen or a lower alkyl radical* It has been found that the compounds according to the invention exhibit strong ineecticidal and acaricidal activities, and have at the same time low toxicity in respect of warm-blooded animals, and low phototoxicity. Their effect sets in rapidly and is long-lasting. The compounds can therefore be used with good success for the control of noxious sucking and biting inseots, Diptera as well as Bites (Acarina).
The invention also consists in processes for the preparation of the oxieecarbamatea of formula I above* By one of thea an oxine of the formula "01"■|>"'p»jf"i" OH is reacted with an isocyanate of the formula Rj H«C m 0 III ae in which formulae R and R^ hare the aame meaningabove.
By another prooeee according to the invention an oxline of formula II is reacted with a carbaaic acid chloride of the formula in which R^ and ^ have the meaning stated above.
In formula I above 6 is preferably an alkyl radical with 1-6 carbon atoms, or a phenyl radical. an alkyl radical with 1-4 carbon atoas and radical with 1-4 carbon atoas.
The first prooeee mentioned above can be Illustrated by the following equation: 0 Cg As examples of ozimee of formula II which can be used, there may b* mentioned α-methylmercapto-, o-ethylmercapto-, a-butylmercapto- and α-dodecylaercapto- as well as a-phenylmercapto-acetaldoxime.
As examples of ieooyanates of formula III there may be mentioned methyl* ethyl and butyl ieocyanate.
The reaction is carried out in the presence of an inert organic solvent* these include, for example, hydrocarbons, such as benain , bensene and toluene, chlorinated hydrocarbons, such as carbon tetrachloride and chlorobeneenes, ethers such as diethyl ether and dioxan, esters such as eth l acetate ketones such as To aocele ate the reaction, there may be added small• amounts of amine, such as triethyl amine, trimethyl amine or dimeth l-aniline.
The reaction temperature may be varied within a wide range* In general, the work ie carried out between 0 and 150°, preferably between 20 and 100°.
In general, approximately equimolecular amounts of the reactants are used. Working up may take place in the usual manner, for example by evaporating the solvent in vacuum or by filtering off the end product with suction, oxime The ege&carbamates are, in general, solid substances which crystallise well* The second process can be illustrated by the following equations 0 O-s— c** —OH + oi — σ —${a&3)2 — > + HC1 The oximes of formula II mentioned above in connection with tht first process are of course also suitable for the second process.
As examples of carbamlc acid chlorides which can be used, there may he mentioned methyl, dimethyl, ethyl and propyl carbamlc acid chloride.
The reaction is preferably effected in the presence of or of the organic solvents mentioned above.
Tor binding the liberated hydrochloric acid, the usual acid-binding agents may he used. Preferred agents include alkali metal hydroxides and alkali metal carbonates, such as sodium The reaction can be effected in the same temperature ranges as stated above.
Approximately equimolecular amounts of the reactants are in general used. The working up of the reaction mixtu e may take place in the usual manner.
As mentioned above, the compounds according to the invention can be used against sucking and biting insects, JJiptera as well as mites (Acarina).
To the sucking insects there belong, mainly, aphids, such as the peach aphid (M eus persicae), the bean aphid (Doralis fabae); scales, such as Aspidiotus hederae, Lecanium hesperidum, Pseudococcus maritimus} Thysanopter , such as hercinothrips femora-lie; and bugs, such as the beet bug (Hesma quadra a) and the bed bug (Cimex lectularius)· The biting insects comprise mainly butterfly caterpillars, such as Plutella maculipennis, Lymantria disparj beetles, such as granary weevils (Sitophilue granarlua), the Colarado beetle (Leptinotarsa -decemlineata) | and also species which live in the soil, such as wlrevorms (Agriotea sp.) and larvae of the cockchafer (Melolontha) ; cockroaches, such as the German cockroach (Blattella germanica)t Orthoptera, such as the house cricket (Gryllus domesti-cus)j termites, such as Setioulltermes; and Hymenoptera, such as ants* The Diptera comprise in particular the flies, such as the vinegar fly (Droeophila melanogaster) , the Mediterranean fruit fly (Ceratitis capitate), the house fly (Musca domestics) and gnats, such ae the mosquito (Aedee aegypti).
In the case of the mites, particularly important are the spider mites (Tetranychidae) , such as the common spider mite (Tetra- nychus urticae), the European red mite (Paratetranychus pilos e);^ blister mites, such as the currant blister mite (Erlophyes rlbls) and tarsonemlds, such as Tarsonemus pal idua; and ticks.
The active compounds according to the invention show, in particular, a strong systemic action and can therefore also be used via, for example, the soil.
The active compounds according to the invention may be converted into the customary formulations, such as solutions, emulsions suspensions, powders, pastes and granulates. These may be prepared in known manner, for example by mixing the active compounds with extenders, i.e. liquid or solid diluents or carriers, optionally with the use of surface-active agents, i.e. emulsifying agents and/or dispersing agents. In the case of the use of water as extender, organic solvents may, for example, also be used as auxiliary solvents.
As liquid diluents or carriers, there are preferably used aromatic hydrocarbons, such as xylenes or benzene, chlorinated aromatic hydrocarbons, such as chlorobenzenes, paraffins, such as mineral oil. fractions, alcohols, such as methanol or butanol, and strongly polar solvents , such as dimethylformamlde or dimethyl- sulphoxide, or water.
As solid diluents or carriers, there are preferably used ground natural minerals , such as kaolins, clays, talcum or chalk, or ground synthetic minerals, such as highly dispersed silicic acid or silicates.
Preferred examples of emulsifying agents include non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alk laryl poly- glycol ethers, alkyl sulphonates and aryl sulphonates. Preferred examples of dispersing agents include lignln, sulphite waste liquors and methyl cellulose.
The active compounds according to the invention may be pre- sent in the formulations in admixture with other active compo nder The formulations contain, in general, from 0.1 to 95, preferably from 0.5 to 90, per cent by weight of active compound.
The active compounds can be used as such, in the form of their formulations or of ready to use preparations made therefrom. Application may take place in customary manner, for example by watering, scattering, dusting or spraying.
The concentrations of active compound can, in use, be varied within a wide range. In general, active compound concentrations of 0.00001-20^, preferably of 0.01-5 , are used for actual application.
The invention therefore also provides an insecticidal or acarlcidal composition containing as active ingredient one of the new oximecarbamates in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
The invention also provides a method of combating insects and acarids which comprises applying to the insects or acarids or a habitat thereof one of the new oximecarbamates alone or In the form of a composition as above.
The insecticidal and acarlcidal activity of the new oximecarbamates is illustrated by the following Examples A-E.
Example A Plutella test Solvent: 3 parts by weight dimethylformamide Emulsifier: 1 part by weight alkylarylpolyglycol ether To produce a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent containing the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) are sprayed with the preparation of the active compound until dew moist and are then in- fee ed with caterpillars of the diamond-back moth (Plutella maculipennle) .
A ter the speci ied periods of time, the degree of destruction is determined as a percentage: lOOjS means that all the caterpillars are killed whereas 0£ means that none of the caterpillars are killed.
The active compounds , the concentrations of the active compounds, the evaluation times and the results can be seen from the following Table: TABLE (plant-damaging insects) Concentration Degree of Active compounds of active destruction compound in after in # 3 days Example B Myzus test (contact action) Solvent: 3 parts by weight dimethyl formamide Emulsifier: 1 part by weight alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent containing the stated amount of emulsifier and the concentrate Is diluted with water to the desired concentration.
Cabbage plants (Brassica oleracea) which have been heavily infested with peach aphlds (Myzus persicae) are sprayed with the preparation of the active compound until dripping wet.
After the specified periods of time, the degree of destruction is determined as a percentage: 100 means that all the aphlds are killed whereas 0% means that none of the aphlds are killed.
The active compounds, the concentrations of the active compounds, the evaluation times and the results can be seen from the following Table: TABLE (plant-damaging insects) Concentration of Degree of Active Compounds active compound destruction in i» in # after 24 hours Example C Rhopalosiphum test (systemic action) Solvent: 3 parts by weight dimethyl formamide Biaulsifier: 1 part by weight alkylaryl polyglycol ether by weight of the active compound is mixed with the stated amoturflV of solvent containing the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
Oat plants (Arena Sativa) which have been strongly infested with oat aphids (Ehopaloslphum padi) are watered with the preparation of the active compound so that the preparation penetrates into the soil without wetting the leaves of the oat plante. (The active compound is taken up by the oat plants from the soil and thus reaches the infested leaves.
After the specified periods of time, the degree of destruction is determined as a percentage: 100 means that all the aphids are killed whereas 0% means that none of the aphids are killed.
The active compounds, the concentrations of the active compounds, the evaluation times and the results can be seen from the following Table: TABLE (plant-damaging insects) Concentration of Degree of Active compounds active compound destruction in J* in ?£· after 2 days CH, 0.2 100 0.02 100 C I = 3 N-0- NH - Concentration of Degree of Active compound active compound destruction in in 56 after 2 days Example D Tetranychus test Solvent: 3 parts by weight dimethyl formamide Emulsifler: 1 part by weight alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent containing the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
Bean plants (Phaseolus vulgaris), which have a height of approximately 10 - 30 cm., are sprayed with the preparation of the active compound until dripping wet. These bean plants are heavily infected with spider mites (Tetranychus telarius) in all stages of development.
After the specified periods of time, the effectiveness of the preparation of active compound is determined by counting the dead mites. The degree of destruction thus obtained is expressed as a percentage: 100 means that all the spider mites are killed whereas 0% means that none of the spider mites are killed.
The active compounds, the concentrations of the active compounds, the evaluation times and the results can be seen from the following Table: TABLE (plant-damaging mites) Concentration of Degree of Active compounds active compound destruction in i» in # after 2 days Example B Laphygma test Solvent: 3 parts by weight acetone Emulslfler: 1 part by weight alkylarylpolyglycol ether To produce a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent containing the stated amount of emulslfler and the concentrate is diluted with water to the desired concentration.
Cotton leaves (Grosaypium barbadense) are sprayed dew-moist with the preparation of the active compound and they are infested with caterpillars of the owlet moth (Laphygima exigua).
After the stated periods of time, the degree of destruction is determined as a percentage: 100J6 means that all the caterpillars are killed whereas 0 means that none of the caterillars are killed.
The active compounds, the concentrations of the active compounds, the evaluation times and the results can be seen from the following Table: (plant-damaging insects) Concentration of Degree of Active compounds active compound destruction in in i» after 3 days (known) The process of the invention is illustrated by the following Examples 1-7.
Example 1 0 C^ - S - C = N- 0 - $ - NHCRj CH^ 11.9 g a-ethylmercapto-acetaldoxime are dissolved in about 150 ml benzene. 6 g methylisocyanate are then added to the solution and, after the addition of 2-3 drops triethylamine, he l s effected for 1 hours after which the recrystallised from ethyl acetate/white spirit. Colourless crystals, m.p. 58°C; yield 14 g.
Example 2 As described in Example 1, 11.9 g of the said oxime in benzene are heated to the boil for 1¼ hours with 7.1 g ethyliso-cyanate and 2 drops trie hylamine. When the clear solution is evaporated, a crystalline residue is obtained which, after recrystal 1 isation from white spirit, melts at 68°C.
Yield about 85 - 90 of the theory.
Example 5 g methylisocyanate and a few drops of triethylamine are added to 74 g a-butylmercapto-acetaldoxime in about 500 ml benzene. The mixture is heated to the boil for 1 - l£ hours. It is then evaporated in a vacuum, and the solid residue is recryetallised from white spirit. About 80 g colourless crystals are obtained; m.p. 73°C C12¾5 - S - C = N - 0 - l- NHCEj CH, j As described in Exemplee 1-3» 13 g 2-dodecylmercapto-acetaldoxime are reacted in 150 ml benzene with 3 g methylisocyanate and 2 drops triethylamine. Working up is effected as described and 13 g colourless crystals are obtained which, after being dissolved in, and allowed to crystallise (without filtra n , CH^ .8 g dimethylcarbamic acid chloride, dissolved in 50 ml.
L6.7 g of benzene, are added dropwise, with stirring, to a solution of / and' 11-g of trimet ylamine u-pfaenylmercapto-acetaldoxime/in 100 ml benzene. This is followed by stirring at boiling temperature for 2-3 hours, filtering off cold with suction and evaporation of the filtrate in a vacuum.
The initially oily distillation residue becomes solid after standing, m.p. 67°C.
Example 7 8 g powdered sodium hydroxide are added in portions, within 15 minutes and at room temperature, to a solution of 23*8 g. a- ethylmercapto-acetaldoxime and 21.5 g dimethylcarbamic acid chloride in 180 cur xylene. This was followed by filtering φ from sodium chloride, and the filtrate was then concentrated. As residue, 37 g carbamate were obtained. m.p. 75 - 77° (after recrystallisation from cyclohexane) In analogy with Examples 1 - 5, the following carbam te was prepared. m.p. 75 - 76c - -
Claims (1)
1. of the formula tt2 which ie an alkyl or phenyl is a lower alkyl and hydrogen or a lower alkyl according to Claim 1 in which is an alkyl radical with 1 6 atoms or a phenyl according to Claim 1 or 2 in which an alkyl radical with t 4 carbon according to any of Claims 1 to 3 or which alkyl radical with 1 4 carbon The of the formula 6k fhe of the formula 0 of the formula 0 ti of the formula 0 The of the formula 0 The of the formula 0 The of the rmula The of the formula She of the formula A process the production of according to of Claims 1 to 15 which an oxiiae of the II 1B reacted with an of the formula in and have th same meaning as in process for production of according to of Claims 1 to 13 in which an of the formula in Claim 14 la reacted with a acid chloride of the formula ox IT in which and have the same meaning in Claim A process according to Claim 14 or 15 in which the reaction ia carried out at 20 to A process according to any of Claims 14 to 16 in which the reaction carried out in the presence of an inert for the production of according to Claim 1 substantially as described herein with reference to Examples 1 to or acarieidal compositions containing aa active ingredient an according to of Claims 1 to 13 in admixture with a liquid diluent or carrier containing a according to Claim 19 containing from to by weight of the active A method of combating insects or aoarida which comprises applying to or acarlde or an insect or habitat an oximecarbamate according to any of Claims 1 to 33 alone or in the form of a composition according to 19 or A method according to Claim 21 in which a composition is used containing to preferably to by weight of the active A according to any of Claims 21 or 22 in whloh the initially applied to soil for growing PARTNERS insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0049058 | 1966-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27735A true IL27735A (en) | 1971-06-23 |
Family
ID=7102695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27735A IL27735A (en) | 1966-04-29 | 1967-04-04 | Oximecarbamates,their preparation and their use as insecticides and acaricides |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE697839A (en) |
| CH (1) | CH480009A (en) |
| DE (1) | DE1568518A1 (en) |
| ES (1) | ES339984A1 (en) |
| FR (1) | FR1521784A (en) |
| IL (1) | IL27735A (en) |
| NL (1) | NL6705984A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1909037C3 (en) * | 1969-02-22 | 1983-12-29 | Metallgesellschaft Ag, 6000 Frankfurt | Process for making solid pellets |
| IT1141219B (en) * | 1980-02-18 | 1986-10-01 | Montedison Spa | PROCESS FOR THE PREPARATION OF N-METHYL-CARBAMATE OF METHYLTHIOACETALDOXY |
| EP0296505A1 (en) * | 1987-06-22 | 1988-12-28 | HENKEL CORPORATION (a Delaware corp.) | Aqueous compositions containing a polymeric fat acid polyamide |
-
1966
- 1966-04-29 DE DE19661568518 patent/DE1568518A1/en active Pending
-
1967
- 1967-04-03 CH CH465067A patent/CH480009A/en not_active IP Right Cessation
- 1967-04-04 IL IL27735A patent/IL27735A/en unknown
- 1967-04-27 NL NL6705984A patent/NL6705984A/xx unknown
- 1967-04-28 BE BE697839D patent/BE697839A/xx unknown
- 1967-04-29 ES ES339984A patent/ES339984A1/en not_active Expired
- 1967-05-02 FR FR104953A patent/FR1521784A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6705984A (en) | 1967-10-30 |
| BE697839A (en) | 1967-10-02 |
| DE1568518A1 (en) | 1970-03-19 |
| FR1521784A (en) | 1968-04-19 |
| ES339984A1 (en) | 1968-05-16 |
| CH480009A (en) | 1969-10-31 |
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