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United States Patent (19) 11 3,941,829 Pissiotas Et Al

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United States Patent (19) 11 3,941,829 Pissiotas Et Al United States Patent (19) 11 3,941,829 Pissiotas et al. (45) Mar. 2, 1976 54 N-PHENYL-N'-CARBOPHENOXY FORMAMIDINES 57 ABSTRACT (75) Inventors: Georg Pissiotas, Lorrach, Germany; Phenylformamidines of the formula Dieter Dürr, Bottmingen, Switzerland 4 R3 (73) Assignee: Ciba-Geigy Corporation, Ardsley, R N.Y. R5 NiccH-N / (22 Filed: Dec. 1, 1972 N (21) Appl. No.: 311,058 COOR2 R6 R7 30 Foreign Application Priority Data Dec. 7, 1971 Switzerland....................... 17790/7 wherein R represents hydrogen, alkyl, alkenyl or al Dec. 7, 1971 Switzerland....................... 1779/7 kynyl, R represents a-naphthyl, Jan. 26, 1972 Switzerland......................... 1224/72 Oct. 27, 1972 Switzerland....................... 5729/72 52) U.S. Cl...... 260f471 C; 260/240 G; 260/465 D; 260/470; 260/472; 424/277; 424/278; 424/285; 424/300 (51) int. Cl......................................... C07C 125/06 (58) Field of Search..... 260/471 C, 472, 470, 240 G 56 References Cited or substituted phenyl, FOREIGN PATENTS OR APPLICATIONS wherein the phenyl group is not substituted simulta 890,922 lf 972 Canada neously in the 2-position by a methyl group and in the 2,202,034 | 972 Germany 4-position by a chlorine atom, R. R. R. R. and R. 2,123,001 81972 France represent one or more radicals which are the same or 778,383 7/1972 Belgium different, such as hydrogen or halogen atoms or alkyl, alkoxy, alkylthio, alkenyloxy, alkynyloxy, alkoxycar Primary Examiner-Anton H. Sutto bonyl, CFs, cyano or nitro groups, their process for Assistant Examiner-Michael Shippen the manufacture and their use in pest control. Attorney, Agent, or Firm-Harry Falber; Frederick H. Rabin; Philip P. Berestecki 6. Claims, No Drawings 3,941,829 1 : 2 N-PHENYL-N'-CARBOPHENOXY FORMAMIDINES Preferred compounds on account of their action are those of the formula I, wherein R represents methyl, The present invention relates to phenylformami R represents o-naphthyl, 5 dines, a process for their manufacture and their use in pest control. The phenyformamidines have the formula 10 COOR2 2-methylphenyl, 3-methylphenyl, 2-chlorophenyl, 2 - 15 isopropylphenyl, 3-isopropylphenyl, 3-methyl-5-iso propylphenyl, 2-chloro-5-tert.butylphenyl, 3,4-dime wherein R, represents hydrogen, alkyl, alkenyl or alky thylphenyl,methyltiophenyl, 3,4,5-trimethylpheryl, 3i Elenji, 3,5-dimethyl-4- 2-isopropox nyl, R, represents o-naphthyl, yphenyl, 2-allyloxyphenyl, 3-methyl-4-dime - 20 thylaminophenyl, 3,5-dimethyl-4-dimethylaminophe nyl, 3,5-dimethyl-4-diallylaminophenyl, i. 1,3-dioxolan 2-yl-phenyl, 1,3-diothiolan-2-yl-phenyl, (4,5-dimethyl 3-dioxolan-2-yl)-phenyl, 3-(1-methylbutyl)-phenyl, 2-sec.butylphenyl, 3-(1-ethylpropyl)-phenyl, 2,3-xylyl, 25 3-tert, butylphenyl, 3-sec.butylphenyl, 3,5-diisopropyl phenyl, 2-chloro-5-isopropylphenyl, 3,5-dimethyl-4- methoxyphenyl, 3-allyloxyphenyl, 2-propargyloxyme or substituted phenyl, thoxyphenyl, 2-Y-methylthiopropylphenyl, 3-(a- wherein the phenyl group is not substituted simulta methoxymethyl)-2-propenylphenyl, 4-(methyl-propar neously in the 2-position by a methyl group and in the 30 gylamino)-3,5-xylyl, 4-(methyl-Y-chloroallylamino)- 4-position by a chlorine atom, R., R., Rs, R and R. 3,5-xylyl, 2-(ethyl-propargylamino)phenyl, 2-chloro represent one or more radicals which are the same or 4,5-dimethylphenyl, 2-(2-propynyloxy)-phenyl, 3-(2- different, such as hydrogen or halogen atoms or alkyl, propynyloxy)-phenyl, 2-dimethylaminophenyl, 2-dial alkoxy, alkylthio, alkenyloxy, alkynyloxy, alkoxycar lylaminophenyl; ' ' 3-methyl-4-dimethylaminome bonyl, CF, cyano or nitro groups. 35 thyleneiminophenyl, 3-dimethylaminome The alkyl, alkyloxy, alkylthio, alkenyl, alkenyloxy, thyleneiminophenyl, 3-isopropyl-4-methylthiophenyl, alkynyl or alkynyloxy groups represented by R and Ra, 5,6,7,8-tetrahydronaphthyl, 2-(methyl-propar R. R., R and R contain l to 18, preferably l to 4, gylamino)-phenyl, 2-(dipropargylamino)-phenyl, 4 carbon atoms in the chain; the alkenyl and alkynyl (dipropargylarnino)-3-tolyl, 4-(dipropargylamino)-3,5- chains contain 3 to 18, preferably 3 to 5, carbon atoms. 40 xylyl, 2-(allyl-isopropylamino)-phenyl, 3-(allyl-iso These groups may be straight-chain or branched, sub propylamino)-phenyl, 3-methoxymethoxy-phenyl, 2 stituted or unsubstituted. Possible substituents are cyclopentylphenyl, 2-(1-butyn-3-yl-oxy)phenyl or 2 halogen atoms. By halogen is meant fluorine, chlorine, (1-methoxy-2-propoxy)-phenyl, Rs, R, Rs, R and R. bromine and/or iodine. Examples of such groups in represent radicals which are the same or different, such clude: methyl, methoxy, methylthio, ethyl, ethoxy, tri .45 as hydrogen, fluorine, chlorine and/or bromine atoms, fluoromethyl, chloroethyl, propyl, isopropyl, n-, i-, sec. or methyl, methoxy, methylthio, trifluoromethyl, and tert. butyl, allyl, methallyl, propargyl, n-butynyl, ethoxycarbonyl, ethylpropyl, isopropyl, n-butyl, al isobutynyl. - lyloxy, propargyloxy, NC or O,N groups, and n is 1 to Possible substituents at the phenyl group represented 3. by R, are chiefly one or more similar or different halo 50 gen atoms, such as fluorine, chlorine, bromine and/or Examples of suitable compounds of the formula I iodine and/or alkyl with 1 to 5 carbon atoms, haloalkyl include: with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon CH. atoms, alkoxyalkyl with 1 to 4 carbon atoms in each of 3 R the moieties, alkylthio with 1 to 4 carbon atoms, al 55 C NCH-N". kynyloxy with 3 to 4 carbon atoms, dialkylamino with 1 N to 4 carbon atoms, dialkenylamino, dialkynylamino, COOR N-alkyl-N-alknylamino, N-alkyl-N-alkenylamino, HO, NC and/or ON groups, as well as cyclopentyl, mo CH noalkylaminomethyleneimino, dialkylaminome 60 3 R thyleneimino, cyclopenityl B cCH-N N COOR O. O. , S S and O O CH 65 3 Rh CHCH CH, N=CH-N 33 N groups. COOR 3,941,829 S 6 in the presence of an acid binding agent. In the formu Cl CH 3 R lae II and III, R to R, have the same meanings as given N=CH-N for the formula I. N Examples of suitable acid binding agents are: for mamidines of the formula II; tertiary amines, such as COOR triethylamine, dimethylaniline, pyridine, inorganic wherein R represents alkyl with 1 to 12 carbon atoms, bases, such as hydroxides and carbonates of alkali and allyl or propargyl, and R represents a-naphthyl, alkaline earth metals, preferably sodium and potassium carbonate. 10 The reaction is carried out preferably in solvents or diluents which are inert towards the reactants. Exam ples of suitable solvents or diluents are: aromatic hy O drocarbons, such as benzene, toluene, benzines, halo 15 genated hydrocarbone, chlorobenzene, polychloroben zenes, bromobenzene, chlorinated alkanes with 1 to 3 carbon atoms; ethers, such as dioxan, tetrahydrofuran; CH CH esters, such as ethyl acetate, ketones, such as methyl ethyl ketone, diethyl ketone, nitriles etc. 2-methylphenyl, 3-methylphenyl, 2-chlorophenyl, 2 20 Some of the starting materials of the formula II and isopropylphenyl, 3-isopropylphenyl, 3-methyl-5-iso III are known compounds which can be manufactured propylphenyl, 2-chloro-5-tert.butylphenyl, 3,4-dime by methods which are known perse. The compounds of thylphenyl, 3,4,5-trimethylphenyl, 3,5-dimethyl-4- the formula I display a broad biocidal activity and can methylthiophenyl, 3,5-di-tert, butylphenyl, 2-iso propoxyphenyl, 2-allyloxyphenyl, 3-methyl-4-dime be used for combating diverse plant and animal pests. thylaminophenyl, 3,5-dimethyl-4-dimethylaminophe 25 In particular, however, they possess insecticidal and nyl, 3,5-dimethyl-4-diallylaminophenyl, 1,3-dioxolan acaricidal properties and may be used against all devel 2-yl-phenyl, 1,3-dithiolan-2-yl-phenyl, (4,5-dimethyl opment states, e.g. eggs, larvae, pupae, nymphs and 1,3-dioxolan-2-yl)-phenyl, 3-(1-methylbutyl)-phenyl, adults, of insects and representatives of the order Aca 2-sec.butylphenyl, 3-(1-ethylpropyl)-phenyl, 2,3-xylyl, rina, for example against insects of the families: 3-tert.butylphenyl, 3-sec.butylphenyl, 3,5-diisopropyl 30 Tettigoniida Tenebrionidae phenyl, 2-chloro-5-isopropylphenyl, 3,5-dimethyl-4- Gryllidae Chrysomelidae methoxyphenyl, 3-allyloxyphenyl, 2-propargyloxyme Gryllor alpidae Bruchidae Blariidae Tineidae thoxyphenyl, 2-Y-methylthiopropylphenyl, 3-(a- Reduviidae Noctuidae methoxymethyl)-2-propenylphenyl, 4-(methyl-propar 35 Phyrrhocoridae Lymatriidae gylamino)-3,5-xylyl, 4-(methyl-Y-chloroallylamino)- Cinicidae Pyralidae Delphacidae Cuicidae 3,5-xylyl, 2-(ethyl-propargylamino)phenyl, 2-chloro Aphidiidae Tipulidae 4,5-dimethylphenyl, 2-(2-propynyloxy)-phenyl, 3-(2- Diaspididae Stonoxydae propynyloxy)-phenyl, 2-dimethylaminophenyl, 2-dial Pseudococcidae Tryperidae lylaminophenyl, 3-methyl-4-dimethylaminome Scarabacidae Muscidae thyleneiminophenyl, 3-dimethylaminome 40 Dernestidae Caliphoridae and thyleneiminophenyl, 3-isopropyl-4-methylthiophenyl, Coccinellidae Pulicidae 5,6,7,8-tetrahydronaphthyl, 2-(methyl-propar gylamino)-phenyl, 2-(dipropargylamino)-phenyl, 4 Acarida of the families: (dipropargylamino)-3-tolyl, 4-(dipropargylamino)-3,5- 45 Ixodidae xylyl, 2-(allyl-isopropylamino)-phenyl, 3-(allyl-iso Argasidae propylamino)-phenyl, 3-methoxymethoxy-phenyl, 2 Tetranychidae and cyclopentylphenyl, 2-(1-butyn-3-yl-oxy)phenyl or 2 Dermanyssidae. (l-methoxy-2-propoxy)-phenyl. The insecticidal and/or acaricidal action can be sub The compounds of the formula I can be manufac 50 stantially broadened and adapted to suit the particular tured by methods which are known per se, e.g. by re circumstances by the addition of other insecticides acting formamidines of the formula and/or
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