Patent GB-1027561-A (GB)
Title: Thiazoline compounds, and pest-controlling agents containing them
IPC: C07D277/38
Filed: 1963-01-01
Abstract: Fertilizers such as calcium cyanamide and urea may be present in pesticidal compositions containing as active ingredient a compound of formula <FORM:1027561/C1/1> in which R1 is phenyl which may be substituted by halogen, CF3, C1- 4 alkyl or alkoxy, or by chlorophenoxy, or R1 is a C1- 12 aliphatic residue; R2 is hydrogen or C1- 4 alkyl; R3 is hydrogen, C1- 4 alkyl or phenyl; and R4 is hydrogen or -COOR5, R5 being C1-4 alkyl, or an acid addition salt thereof (see Division A5).ALSO:Pesticidal compounds of the formula (see Division A5) <FORM:1027561/C2/1> in which R1 is phenyl which may be substituted by halogen, CF3, alkyl or alkoxy of 1-4 carbon atoms, or by chlorophenoxy, or R1 is a C1- 12 aliphatic residue; R2 is hydrogen or C1- 4 alkyl; R3 is hydrogen, C1- 4 alkyl or phenyl; and R4 is hydrogen or -COOR5, R5 being C1- 4 alkyl, are prepared by (a) rection of a monosubstituted thiourea with an a -halo-carbonyl compound, followed by alkylation if required; or (b) reaction of an N,N1-disubstituted thiourea with an a -halocarbonyl compound. A non-polar solvent such as toluene may be employed; the products are obtained as hydrohalides; the free bases or other salts may also be prepared.  Compounds of the above formula in which R1 is phenyl substituted by at least 2 halogen atoms or C1- 4 alkyl radicals, or by one or more CF3 or C1- 4 alkoxy radicals, or by chlorophenoxy, or is allyl or dodecyl, and their acid addition salts, are claimed as novel.ALSO:Pest combating preparations contain as active ingredient a compound of formula <FORM:1027561/A5-A6/1> in which R1 is phenyl which may be substituted by one or more halogen atoms, CF3, C1-4 alkyl or alkoxy, or by chlorophenoxy, or R1 is a C1-12 aliphatic residue; R2 is hydrogen or C1-4 alkyl; R3 is hydrogen, C1-4 alkyl or phenyl; R4 is hydrogen or -COOR5, R5 being C1-4 alkyl; or an acid addition salt thereof (see Division C2); together with, if desired, a diluent, solvent, wetting agent, emulsifier, adhesive, fertilizer, or other pesticide.  Other pesticides specified are herbicides such as tri- and tetra-substituted arylalkyl ureas, halophenoxyalkanoic acids, halogenated benzoic and phenylactic acids and halogenated fatty acids and salts, esters and amides thereof, chlorinated hydrocarbons, phosphoric acid esters, tertiary or quaternary amines such as dodecyl hexamethylene-imine and its salts and 1,11-ethylene-2,21-dipyridinium dibromide, carbamates, thiolcarbamates, dithiocarbamic acid esters, s-triazine derivatives, 2-chlorobenzthiazole, 3-amino-1, 2, 4-triazole, maleic acid hydrazide, 3, 5-dimethyltetrahydro-1, 3, 5-thiadiazine-2-thione, pentachlorophenol, dinitrocresol, dinitrobutylphenol, naphthylphthalamic acid and methyl isothiocyanate; and bactericides, fungicides and nematocides. Other additives specified are borax, abraum salts, calcium cyanamide, urea; organic solvents; cationic, anionic or non-ionic emulsifiers; talcum, kaolin, bentonite, calcium carbonate, calcium phosphate, coal, cork meal, wood meal; and fatty acids, resins, glue, casein and alginates.  An example also incorporates silicic acid.