The title compound, useful as an insecticide.

DESCRIPTION OF THE INVENTION 
It has been found that useful insecticidal activity is possessed by 
3-acetyltetrahydro-2-(nitromethylene)-2H-1,3-thiazine, which can be 
described by the general formula 
##STR1## 
The compound of the invention can be prepared as follows: 
A solution of 23 g of 
1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-pentanone (Example 5, 
U.S. Pat. No. 3,962,225) in 200 ml of monoglyme was added dropwise at 
0.degree. C to a suspension of 4.65 g of a 57% sodium hydride/mineral oil 
dispersion in 100 ml of monoglyme. The stirred mixture was allowed to warm 
to room temperature and stirred overnight. A solution of 8.2 g of acetyl 
chloride in 50 ml of monoglyme was added dropwise to the reaction mixture 
at 0.degree. C. The resulting mixture was stirred for one hour at 
0.degree. C, then allowed to warm to room temperature and stirred for 30 
minutes. The mixture was diluted with chloroform and extracted with 10% 
sodium hydroxide solution. The organic phase was separated, washed with 
water, then with saturated sodium chloride solution, and dried (Na.sub.2 
SO.sub.4), and the solvent was evaporated under reduced pressure. The 
resulting liquid was chromatographed, using a wet column with silica gel. 
As eluent, there was first used 2 liters of a 98/2 chloroform/acetone 
mixture, then a 95/5 chloroform/acetone mixture was used. Three fractions 
were obtained. The last fraction was triturated with ether, then cooled, 
to give a solid yellow product, the compound of this invention, m.p.: 
91.degree.-92.5.degree. C. The identity of the product was confirmed by 
appropriate chemical and spectral analyses. 
The compound of this invention exhibits useful insecticidal activity, being 
of particular interest for control of the larvae "caterpillar" or "worm" 
forms of insects of the genus Heliothis, such as H. Zea (corn earworm, 
cotton bollworm, tomato fruitworm), H. virescens (tobacco budworm); the 
genus Agrotis, such as A. ipsilon (black cut-worm); the genus 
Trichoplusia, such as T. ni (cabbage looper), and the genus Spodoptera, 
such as S. littoralis (Egyptian cotton leafworm). It also is of interest 
for controlling aphids and houseflies. In tests that have been conducted 
it has exhibited low, or no, toxicity to other insects such as the 
2-spotted spider mite and mosquito larva. It acts rapidly on corn earworm 
larvae, houseflies and pea aphids, providing "quick knock-down" of these 
insects. 
Activity of the compound of this invention with respect to insects was 
determined by using standardized tests to establish the LC.sub.50 dosage 
(in milligrams of test compound per 100 milliliters of solvent or liquid 
carrier required in the solution or suspension of the compound) that was 
required to kill 50% of the test insects. The test insects were the 
housefly, corn earworm, mosquito, pea aphid and 2-spotted spider mite. 
The compound was found to be inactive or but slightly active with respect 
to the mites and mosquito larvae. It was found to be highly active with 
respect to the corn earworms and moderately active with respect to the pea 
aphids and houseflies. 
In the course of these tests it was noted that the compound acted quickly 
on the houseflies, pea aphids and corn earworms. 
The invention includes within its scope insecticidal compositions 
comprising an adjuvant -- that is, a carrier optionally a surface-active 
agent -- and, as active ingredient, the compound of this invention. 
Likewise the invention includes also a method of combatting insect pests 
at a locus which comprises applying to the locus an effective amount of 
the compound of the invention. 
The term "carrier" as used herein means a material which may be inorganic 
or organic and of synthetic or natural origin with which the active 
compound is mixed or formulated to facilitate its application to the 
plant, seed, soil and other object to be treated, or its storage, 
transport or handling. The carrier may be a solid or a liquid. 
Suitable solid carriers may be natural and synthetic clays and silicates, 
for example, natural silicas such as diatomaceous earths; magnesium 
silicates, for example, talcs; magnesium aluminum silicates, for example, 
attapulgites and vermiculites; aluminum silicates, for example, 
kaolinites, montmorillonites and micas; calcium carbonate; calcium 
sulfate; synthetic hydrated silicon oxides and synthetic calcium or 
aluminum silicates; elements such as for example, carbon and sulfur; 
natural and synthetic resins such as for example, coumarone resins, 
polyvinyl choride and styrene polymers and copolymers, solid 
polychlorophenols; bitumen, waxes such as beeswax, paraffin wax and 
chlorinated mineral waxes; degradable organic solids such as ground corn 
cobs and walnut shells and solid fertilizers, for example, 
superphosphates. 
Suitable liquid carriers include solvents for the compounds of this 
invention and liquids in which the toxicant is insoluble or only slightly 
soluble. 
Examples of such solvents and liquid carriers generally are water, 
alcohols, for example, isopropyl alcohol, ketones, such as acetone, methyl 
ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers, aromatic 
hydrocarbons, such as benzene, toluene and xylene; petroleum fractions, 
such as kerosene, light mineral oils, chlorinated hydrocarbons, such as 
carbon tetrachloride, perchlorethylene, trichloroethane, including 
liquefied normally vaporous gaseous compounds. Mixtures of different 
liquids are often suitable. 
If used, the surface-active agent may be an emulsifying agent or a 
dispersing agent or a wetting agent. It may be nonionic or ionic. 
Surface-active agents usually applied in formulating pesticides may be 
used. Examples of such surface-active agents are the sodium or calcium 
salts of polyacrylic acids and lignin sulfonic acids; the condensation 
products of fatty acids or aliphatic amines or amides containing at least 
12 carbon atoms in the molecule with ethylene oxide and/or propylene 
oxide; fatty acid esters of glycerol, sorbitan, sucrose or 
pentaerythritol; fatty acid salts of low molecular weight, mono-, di- and 
trialkylamines; condensates of these with ethylene oxide and/or propylene 
oxide; condensation products of fatty alcohols or alkyl phenols, for 
example, p-octylphenol or p-octylcresol, with ethylene oxide and/or 
propylene oxide; sulfates or sulfonates of these condensation products; 
alkali or alkaline earth metal salts, preferably sodium salts, of sulfuric 
or sulfonic acids esters containing at least 10 carbon atoms in the 
molecule, for example, sodium lauryl sulfate, sodium secondary alkyl 
sulfates, sodium salts of sulfonated caster oil, and sodium alkyaryl 
sulfonates such as sodium dodecylbenzene sulfonate; and polymers of 
ethylene oxide and copolymers of ethylene oxide and propylene oxide. 
The compositions of the invention may be formulated as wettable powders, 
dusts, granules, solutions, emulsifiable concentrates, emulsions, 
suspension concentrates or aerosols. Encapsulated formulations and 
controlled release formulations also are contemplated, as are bait 
formulations. Wettable powders are usually compounded to contain 25, 50 or 
75%w of toxicant and usually contain, in addition to solid carrier, 3-10%w 
of stabilizer(s) and/or other additives such as penetrants or stickers. 
Dusts are usually formulated as a dust concentrate having a similar 
composition to that of a wettable powder but without a dispersant, and are 
diluted in the field with further solid carrier to give a composition 
usually containing 1/2-10%w of toxicant. Granules may be manufactured by 
agglomeration or impregnation techniques. Generally, granules will contain 
1/2-25%w toxicant and 0-10%w of additives such as stabilizers, slow 
release modifiers and binding agents. Emulsifiable concentrates usually 
contain, in addition to the solvent, and when necessary, co-solvent, 
10-50%w/v toxicant, 2-20%w/v emulsifiers and 0-20%w/v of appropriate 
additives such as stabilizers, penetrants and corrosion inhibitors. 
Suspension concentrates are compounded so as to obtain a stable, 
non-sedimenting, flowable product and usually contain 10-75%w toxicant, 
0-5%w of dispersing agents, 0.1-10%w of suspending agents such as 
protective colloids and thixotropic agents, 0-10%w of appropriate 
additives such as defoamers, corrosion inhibitors, stabilizers, penetrants 
and stickers, and as carrier, water or an organic liquid in which the 
toxicant is substantially insoluble; certain organic additives or 
inorganic salts may be dissolved in the carrier to assist in preventing 
sedimentation or as antifreeze agents for water. 
Aqueous dispersions and emulsions, for example, compositions obtained by 
diluting a wettable powder or an emulsifiable concentrate according to the 
invention with water, also lie within the scope of the present invention. 
The compositions of the invention may also contain other ingredients, for 
example, other compounds possessing pesticidal, herbicidal or fungicidal 
properties, or attractants, such as pheromones, attractive food 
ingredients, and the like, for use in baits and trap formulations. 
These compositions are applied in sufficient amount to supply the effective 
dosage of toxicant at the locus to be protected. This dosage is dependent 
upon many factors, including the carrier employed, the method and 
conditions of application, whether the formulation is present at the locus 
in the form of an aerosol, or as a film, or as discrete particles, the 
thickness of film or size or particles, the insect species to be 
controlled and the like, proper consideration and resolution of these 
factors to provide the necessary dosage of active material at the locus 
being within the skill of those versed in the art. In general, however, 
the effective dosage of toxicants of this invention at the locus to be 
protected -- i.e. the dosage to which the insect contacts -- is of the 
order of 0.001% to 0.5% based on the total weight of the formulation, 
though under some circumstances the effective concentration will be as 
little as 0.0001% or as much as 2%, on the same basis.