Pesticidal phosphoroamido(di)thioates

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to novel phosphoroamidothioate and phosphoroamidodithioate compounds, to compositions thereof which are useful as pesticides, for example, as arthropodicides (that is, insecticides and acaricides), nematocides, and fungicides, and to a method of controlling pests, such as insects, acarids, nematodes, and fungi. The compounds are effective when applied by soil application techniques and by foliar application techniques.
2. Description of the Prior Art
Ollinger, U.S. Pat. No. 4,263,288, issued Apr. 21, 1981, discloses acaricidal, insecticidal, and nematocidal phosphoroamidothioates having the formula
[(A--N.dbd.C(R)](N(R.sup.1)]P(.dbd.X)(R.sup.2)(SR.sup.3)
wherein
A is aryl,
R is hydrogen or alkyl,
R.sup.1 is alkyl, cycloalkyl, alkenyl, alkynyl or aralkyl,
R.sup.2 is alkylthio, aryloxy, or amino,
R.sup.3 is alkyl, and
X is O or S.
The several Magee patents, U.S. Pat. Nos. 3,716,600, 4,049,679 (and continuation-in-part thereof, 4,110,443), 3,914,417, 3,845,172, 3,885,032, and 3,825,634, disclose insecticidal phosphoroamidothioates and phosphoroamidodithioates and methods of killing insects therewith. Column 18, lines 1-8 of U.S. Pat. No. 3,716,600 discloses broadly that, in addition to foliar application of the insecticidal compounds, one or more of the compounds may be applied in other liquid or solid formulations to the insects, their environment or hosts, for example, directly to plants or soil so as to effect control of insects coming into contact therewith. The compounds have the formula
(RY)(R.sup.1 S)P(.dbd.O)(N(R.sup.3)(C(.dbd.O)R.sup.2)
wherein R, R.sup.1, R.sup.2, and R.sup.3, respectively, broadly, are alkyl, alkenyl, alkynyl, and haloalkyl, and Y is O or S.
The abstract of Japanese Pat. No. 77012251 discloses N--acyl--O--alkyl--S--alkyl(alkoxy, alkylthio, alkenyl, phenyl, alkoxycarbonyl, cyano, carbamoyl)--phosphoroamidothioates having insecticidal activity and having the formula
[(R.sup.2 C(O)--N(H)]P(.dbd.O)(OR.sup.1)(S(CH.sub.2).sub.n R.sup.3).
Osborne, U.S. Pat. No. 3,399,213, discloses parasiticidal and fungicidal acylphosphoroamidate compounds having the formulas
(G)(G)P(.dbd.Z)[N(G"')--C(.dbd.O)--G"--C(.dbd.O)-[OG']
and
(G)(G)P(50 Z)[N(O)--C(.dbd.O)--G"--O]
wherein G represents lower alkylamino, alkoxy, alkylthio, alkylphenyl, phenoxy, and substituted phenyl.
Braxton, Jr., et. al., U.S. Pat. No. 3,511,635, discloses herbicidal organophosphorous--nitrogen compounds having the formula
(R.sup.1)P(.dbd.X.sup.1)(--XR.sup.2)(.dbd.N(CH.sub.2).sub.n)
wherein
R.sup.1 and R.sup.2 are alkyl, alkenyl, diaryl, alkaryl, or aralkyl groups;
X and X.sup.1 are O, S, or Se; and
n is an integer from 2-9.
Kishino et. al., U.S. Pat. No. 3,760,043, disclose O--phenyl--S--alkyl--N--alkyl--phosphoroamidothioates which possess fungicidal, acaricidal, insecticidal, and nematocidal properties and have the formula
Aryl--O--P(.dbd.O)(NHR.sup.1)(SR.sup.2).
Schroeder, U.S. Pat. No. 3,657,426, discloses a method of controlling nematodes and other parasitic worm life existing in the soil at some stage of its life cycle by applying to the pests to be controlled or to the soil in which they live an effective amount of an O,O--dialkyl O-(1,2-dihydro-2-keto-1,6-dialkyl-4-pyridyl)phosphorothionate having the formula ##STR1##
Although the prior art discloses phosphoroamidothioate and phosphoroamidodithioate compounds having pesticidal, including insecticidal, activity, there remains a need for pesticidal compounds having improved pesticidal efficacy, and diminished detrimental effects such as mammalian toxicity and environmental waste, especially against soil insects such as the corn rootworm.
The prior art, including the several Magee patents described above which constitute the closest art known, do not provide any specific teaching illustrative of the insecticidal activity of the compounds therein disclosed when applied in the soil to protect against soil organisms. It is well known to those skilled in the art that organophosphates having a high order of contact insecticidal efficacy when applied to aerial, or foliar, portions of plants offer relatively little economic value as plant protectants when applied, or introduced, into the soil environment of the plants. Organophosphates tend to be susceptible to rapid degradative processes in the soil due to the combination of such factors as the hydrolytic action of soil moisture, unfavorable soil pH conditions, both of the above being exacerbated by the presence of soil microflora and fauna capable of rendering the insecticidal compound inactive. Application of a pesticide to the soil in ordinary agricultural practice does not necessarily or usually coincide with the presence of susceptible life stages of the target pest. For example, the hatching of insect eggs may be either delayed or it may occur over an interval of several days to several or many weeks. Insect ova are not generally affected by organophosphate pesticides. Thus, pesticidal compounds having satisfactory residual activity, especially in the soil--pesticidal compounds that retain their pesticidal efficacy under atmosphere conditions over an interval of several days to several or many weeks--are required in order to assure satisfactory protection of plants against soil insects. Further, it is highly desirable that such pesticidal compounds having activity persistent over an interval of several days to several or many weeks elicit control over a diverse selection of soil organisms that are agricultural pests.
SUMMARY OF THE INVENTION
It is an object of the invention to provide compounds, and compositions thereof, which are effective as pesticides, for example, as arthropodicides (including insecticides and acaricides), as nematocides, and as fungicides when applied by soil application or by foliar application techniques, especially against soil insects, for example the corn rootworm, and to provide a method for controlling said pests.
These and other objects as will become apparent, achieved by the present invention which comprises ##STR2## wherein: R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be from one to four of the same or different bromo, chloro or fluoro groups;
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)alkynyl;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms or, when X and Y are both S, CH.sub.3 ; or
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)alkynyl;
(C.sub.3 -C.sub.6)cycloaliphatic or heterocycloaliphatic;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.3 is hydrogen;
methyl;
trifluoromethyl;
carbo(C.sub.1 -C.sub.4)alkoxy; or
thiocarbo(C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is hydrogen;
unsubstituted or substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; unsubstituted or substituted (C.sub.3 -C.sub.4)alkenyl wherein the substituent can be from one to three of the same or different phenyl, alkyl, carbo(C.sub.1 -C.sub.4)alkoxy, bromo, chloro or fluoro groups;
(C.sub.3 -C.sub.6)alkynyl;
unsubstituted or substituted phenyl wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl, or naphthyl, (C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, benzyloxy, methylenedioxy, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
X, Y and Z are independently O or S provided that both X and Y are not O at the same time except that, in the case that X and Y are both O and Z is S, then R.sup.1 is n--C.sub.3 H.sub.7 or s--C.sub.4 H.sub.9, R.sup.2 is s--C.sub.4 H.sub.9, R.sup.3 is H, and R.sup.4 is CH.sub.3.
In another aspect, this invention comprises a pesticidal composition, especially an insecticidal composition comprising a pesticidally effective amount of the compound of the invention defined herein above.
In yet another aspect, this invention comprises a method of controlling pests, insects, nematodes, acarids, and fungi, especially soil insects and pests, which comprises applying to the pests, insects, nematodes, acarids and fungi comprising applying on or in the soil or to the loci of plants to be freed from infestation a pesticidally or insecticidally effective amount of an active compound having the formula (I) defined herein above, or of a compound of formula (I) above except that X, Y and Z are independently O or S wherein X and Y may both be O at the same time.
In the practice of the method of the invention, the active compound may be applied to the soil, absorbed by plants grown in the soil, and ultimately ingested by the pests, insects, nematodes, acarids or fungi by means of ingestion of the plant part(s). This means of application is referred to as "systemic" application. Alternatively, the active compound may be applied to the soil and contacted therein with the insects and other pests to be controlled. This means of application is referred to as "soil" application. In another alternative the active compound may be foliarly applied to the plants to be freed from insects and other pests.
When using the compounds defined above, the method of the invention is especially effective against soil insects when the active compound is applied on or in the soil in order to effect direct contact with the insects or other pests, including nematodes, acarids and fungi. By "pests" is meant organisms including arthropods, which in turn includes insects and acarids, nematodes, and fungi, which organisms attack agricultural plants.
In a preferred embodiment for soil application, this invention comprises a compound according to formula (I) wherein:
R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)cycloaliphatic or heterocycloaliphatic;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.3 is hydrogen;
methyl; or
trifluoromethyl; and
R.sup.4 is hydrogen;
unsubstituted or substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)alkynyl;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl lring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms.
In a more preferred embodiment for soil application, this invention comprises a compound according to formula (I) wherein:
R.sup.1 is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl;
R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl or benzyl;
R.sup.3 is hydrogen, methyl, or trifluoromethyl; and
R.sup.4 is methyl, ethyl, n--propyl, propenyl or unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups.
In a most preferred embodiment for soil application, this invention comprises a compound according to formula (I) wherein:
R.sup.1 is methyl, ethyl, or 2,2,2-trifluoroethyl;
R.sup.2 is n--propyl, 3-pentyl, or 1-methylpropyl;
R.sup.3 is hydrogen;
R.sup.4 is methyl, ethyl, or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups;
X and Y are, independently, O or S; and
Z is O.
Especially preferred embodiments of this invention comprise compounds having the following formulas:
(H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHO));
(H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS));
(H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(CH.sub.3)(CHO));
(H.sub.5 C.sub.2 O)P(O)(S sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS)); and
(H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 CF.sub.3 --3)(CHO)).
The development of the class of compounds described above led to the preparation of analogous compounds which were found to possess advantageous pesticidal efficacy when applied to agricultural plants by foliar application techniques. In a preferred embodiment for foliar application, the invention comprises a compound having the formula ##STR3## wherein: R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be one (C.sub.1 -C.sub.4)alkoxy or from one to three of the same or different bromo, chloro or fluoro groups;
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)alkynyl;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.2 is unsubstituted or substituted C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same of different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)alkynyl;
(C.sub.3 -C.sub.6)cycloaliphatic or heterocycloaliphatic;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.3 is hydrogen;
R.sup.4 is substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different phenylcarbonyl, carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
unsubstituted or substituted (C.sub.3 -C.sub.6)alkenyl wherein the substituent can be from one to three of the same or different phenyl, carbo(C.sub.1 -C.sub.4)alkoxy, bromo, chloro or fluoro groups;
(C.sub.3 -C.sub.6)alkynyl;
unsubstituted or substituted phenyl, or naphthyl, (C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkyamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; and X, Y and Z are each O.
In a more preferred embodiment for foliar application, this invention comprises a compound according to formula (I) wherein
R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)cycloaliphatic or heterocycloaliphatic;
unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkythio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups; wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
R.sup.3 is hydrogen;
R.sup.4 is substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, alkylthio, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
(C.sub.3 -C.sub.6)alkenyl;
(C.sub.3 -C.sub.6)alkynyl;
unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substitutent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;
In a most preferred embodiment for foliar application, this invention comprises a compound according to formula (I) wherein
R.sup.1 is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl, or benzyl;
R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl, or benzyl;
R.sup.3 is hydrogen; and
R.sup.4 is unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups.
In an especially preferred embodiment for foliar application, this invention comprises a compound according to formula (I) wherein:
R.sup.1 is methyl, ethyl, or 2,2,2-trifluoroethyl;
R.sup.2 is n--propyl, 3-pentyl, or 1-methylpropyl;
R.sup.3 hydrogen; and
R.sup.4 is unsubstituted or substituted benzyl wherein the substituent can be from one to two (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups.
Compounds illustrative of the invention include the following:
N-methyl-N-hydrogenthiocarbonyl-O-ethyl-S-n-butyl phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-butyl phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-n-butyl phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(1-pentyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(3-nitropropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-nitro propyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-fluoroethyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl)phosophoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthiomethyl phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthioethyl phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-ethylthiomethyl phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidothioate
N-methyl N-hydrogencarbonyl O-ethyl S-(3-butenyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(2-butenyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(5-hexenyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-propargyl phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-phenyl phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-ethyl S-(5-phenyl-1-pentyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-phenyl-1-pentyl)phosphoroamidodithioate
N-methyl N-methylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-butylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-heptyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-methoxypropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-(3-methoxypropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-methoxylpropyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-chloropropyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-chloropropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-(3-chloropropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(2-fluoroethyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-(2-fluoroethyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(2-butenyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(2-butenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-(2-butenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(5-hexenyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(5-hexenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(5-hexenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothiaote
N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1 methylpropyl)phosphoroamidothioate
N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-[(2-carboethoxy)-1-propenyl]N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-hexyn-1-yl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-hexyn-1-yl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(3-hexyn-1-yl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-phenyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-p-chlorobenzyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(5-phenyl-1-pentyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-(5-phenyl-1-pentyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
N-(5-phenyl-1-pentyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl-O-propyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-propyl S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-propyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-(2,2,2-trifluoroethyl)S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl)S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl)S-1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-allyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-allyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarobnyl O-allyl S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarobnyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-(3-hexyn-1-yl)S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-(3-hexyn-1-yl)S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-phenyl S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-phenyl S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-pheny S-(1methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogencarbonyl O-(2-phenylethyl)S-(1-methylpropyl)phosphoroamidodithioate
N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl)S-(1-methylpropyl)phosphoroamidothioate
N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl S-(1-methylpropyl)phosphoroamidodithioate
S,S'-dibutyl N-hydrogenthiocarbonyl N-methyl phosphoroamidodithioate
N-hydrogencarbonyl N,S-dimethyl S'-(1-methylpropyl)phosphoroamidotrithioate
N-methylthiocarbonyl N,S,S'-tripropyl phosphoroamidodithioate
S-ethyl N-heptyl S'-propyl N-trifluoromethylcarbonyl phosphoroamidotrithioate
S-methyl S'-pentyl N-propyl N-propoxymethylthiocarbonyl phosphoroamidodithioate
S-ethyl S'-(2-hexenyl)N-methyl N-trifluoromethylthiocarbonyl phosphoroamidotrithioate
N-ethyl S-methyl S'-(2-propenyl)N-trifluoromethyl phosphoroamidotrithioate
N-ethyl N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl)phosphoroamidodithioate
N-ethyl N-hydrogenthiocarbonyl S-(1-methylpropyl)S'-(2-propynyl)phosphoroamidotrithioate
N-ethyl S-(2-hexynyl)N-hydrogencarbonyl S'-(1-methylpropyl)phosphoroamidotrithioate
S-(2-fluorobutyl)N-hydrogenthiocarbonyl N-methyl S'-(1-methylethyl)phosphoroamidodithioate
N-methylcarbonyl S-phenyl N,S'-dipropyl phosphoroamidodtrithioate
S-benzyl S'-(1-ethylpropyl)N-hydrogenthiocarbonyl N-methyl phosphorotriamidothiate
S-butyl N-ethyl N-methylcarbonyl S'-(5-phenylpentyl)phosphoroamidotrithioate
S-butyl N-methylthiocarbonyl N-(2-propenyl)S'-propyl phosphoroamidodithioate
N-(3-hexenyl)N-hydrogencarbonyl S,S'-dipropyl phosphoroamidotrithioate
N-(3-hexynyl)N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl)phosphoroamidodithioate
S-ethyl N,S'-di-(3-propynyl)N-trifluoromethylthiocarbonyl phosphoroamidodithioate
N-benzyl N-hydrogenthiocarbonyl S,S'-dipropyl phosphoroamidotrithioate
N-(carbomethoxymethyl)-N-hydrogencarbonyl O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-(carboethoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-(cyanomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate
N-(methoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-(methylthiomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-butyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-4-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-3-methoxybenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-3-trifluoromethylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-4-chlorophenylthiomethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-3-phenyl-2-butenyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate
N-1-methylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-4-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-4-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-phenyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate
N-4-chlorophenoxymethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-1-naphthylmethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-2-bromobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate
N-2-chloro-6-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-4-methylthiobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate
N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-2-chloro-6-fluorobenzyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-3-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-2-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
N-3-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidothioate
N-3-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate
The method of controlling arthropods, including insects, nematodes, acarids, other pests, and fungi, according to the invention, comprises applying directly to the insects, nematodes, acarids, other pests and fungi or to the loci to be freed or protected from attack by the arthropods--insects, nematodes, acarids, other pests and fungi--an arthropodocidally effective amount of an active compound having the formula (I) defined hereinabove except that X, Y and Z are independently O or S.
In one preferred aspect, the method of the invention comprises applying on or in the soil an arthropodocidally or pesticidally or fungicidally effective amount of the active compound having the formula (I) above wherein:
R.sup.1 is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl;
R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl or benzyl;
R.sup.3 is hydrogen;
R.sup.4 is methyl, ethyl, n--propyl, propenyl, or unsubstituted or substituted benzyl; and
X, Y and Z are, independently, O or S.
The following compounds are illustrative of the more preferred group of compounds useful by soil application techniques:
(H.sub.5 C.sub.2 O)P(O)(S--n--C.sub.3 H.sub.7)(N(C.sub.2 H.sub.5)(CHO));
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHO));
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS));
(H.sub.2 C.sub.2 O)P(O)(S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHO));
(H.sub.2 C.sub.2 O)P(O)(S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHS));
(H.sub.5 C.sub.2 O)P(S) (S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHO));
(H.sub.5 C.sub.2 O)P(S)(S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHS))
(H.sub.5 C.sub.2 O)P(O)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.3)(CHS))
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 CF.sub.3)(CHO))
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 CH.dbd.CH.sub.2)(CHO)); and
(H.sub.5 C.sub.2 O)P(O)(S--3--pentyl)(N(C.sub.2 H.sub.5)(CHS)).
Especially preferred the method of the invention are the following compounds:
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHO));
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS)); and
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.3)(CHO)).
In another preferred aspect, the method of the invention comprises applying to agricultural plants for foliar application techniques, an arthropodically or pesticidally or fungicidally effective amount of the active compound having the formula (I) above wherein:
R.sup.1 is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl or benzyl;
R.sup.2 is unsubsitutued straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl, or benzyl;
R.sup.3 is hydrogen;
R.sup.4 is unsubstituted or substituted alkyl or unsubstituted or substituted benzyl; and
X, Y, and Z are each O.
The following compounds are illustrative of the more preferred groups of compounds useful by foliar application techniques:
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 CN--4)(CHO))
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9 )(N(CH.sub.2 C.sub.6 H.sub.4 F--4)(CHO))
Especially preferred n the foliar application method of the invention are the compounds:
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 CN--4)(CHO))
(H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 NO.sub.2 --4)(CHO))
The compounds useful according to this invention can be obtained by several reaction sequences. One method for the preparation of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves conversion of S-alkyl phosphorodichlorothioates to the products in four or five steps as is illustrated by the following reaction scheme: ##STR4##
Another method for the preparation of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves the S-alkylation of suitably substituted salts according to the following reaction: ##STR5##
The product of this alkylation reaction having the formula (IV) can then be further treated as illustrated in the reaction scheme set forth above to obtain the new compounds of the invention having the formula (VIII) and (XI).
Still another method for the preparaton of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves the reaction of diethyl chlorophosphite with a suitably substituted sulfenyl halide to obtain an intermediate O,S-disubstituted phosphorochloridothioate, corresponding to formula (III), designated below by the formula number (III'), in the reaction scheme set forth above, as follows: ##STR6##
Intermediate (III') can be further reacted as set forth in the reaction scheme illustrated above to obtain the desired end products.
Yet another method for the preparation of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves the N-alkylation in the presence of a suitable base of a hydrogencarbonyl phosphoroamido(di)thioate according to the following reaction: ##STR7##
The product of this reaction having the formula (VI) can be further reacted as set forth in the reaction scheme illustrated above to obtain the hydrogenthiocarbonyl phosphoroamido(di)thioate compound having the formula (VIII).
The S,S-dialkyl phosphoroamidodithioates of the invention can be prepared according to the following sequence: ##STR8##
For use as pesticides, the compounds of this invention can be used as solutions, suspensions, or mixtures, in organic solvents or formulations. For example, they can be formulated as wettable powders, emulsifiable concentrates, dusts, granular formulations or flowable emulsifiable concentrates. In such formulations, the compounds of this invention are present at a concentration of about 0.00001 to about 99%, preferably about 1 to about 95%, and are extended with an agronomically acceptable liquid or solid carrier. When desired, suitable surfactants are likewise incorporated. Surfactants commonly used in the art can be found in the John W. McCutcheon, Inc. publication "Detergents and Emulsifiers Annual."
By "agronimically acceptable carrier" is meant any substance which can be utilized to dissolve, disperse or diffuse the chemical incorporated therein without impairing the effectiveness of the toxic agent and which does not create permanent damage to such environment as soil, equipment, and agronomic crops when utilized according to recommendations.
The compounds of this invention can be taken up on or mixed with a finely particled solid carrier, as for example, clays, inorganic silicates, carbonates, and silicas. Organic carriers can also be employed.
Dust concentrates are commonly made wherein compounds are present in the range of about 20 to 80%. For ultimate applications, these concentrates are normally extended with additional solid to given an active ingredient content of from 1 to about 20%. Granular formulations are being made using a granular or pelletized form of carrier, such as granular clays, vermiculite, charcoal or corn cobs, and may contain the active ingredient from about 1 to about 25% by weight.
Wettable powder formulations are made by incorporating the compounds of this invention in an inert, finely divided solid carrier along with a surfactant which can be one or more elulsifying, wetting, dispersing, or spreading agents or a blend of these. The compounds are usually present in the range of about 10 to about 80% by weight and surfactants in from about 0.5 to about 10% by weight. Commonly used emulsifying and wetting agents include polyoxyethylated derivatives of alkylphenols, fatty alcohols, fatty acids, alkylamines, alkylarene sulfonates and dialkyl sulfosuccinates. Spreading agents include such material as glycerol mannitan laurate and a condensate of polygylcerol and oleic acid modified with phthalic anhydride. Dispersing agents include such materials as the sodium salt of the copolymer of maleic anhydride and an olefin such as diisobutylene, sodium lignin sulfonate and sodium formaldehydenaphthalene sulfonates.
One convenient method for preparing a solid formulation is to impregnate the compounds of this invention onto the solid carrier by means of a volatile solvent, such as acetone. In this manner, adjuvants, such as activators, adhesives, plant nutrients, synergists and various surfactants can also be incorporated.
Emulsifiable concentrate formulations are prepared by dissolving the compounds of this invention in an agronomically acceptable organic solvent and adding a solvent-soluble emulsifying agent. Suitable solvents are usually water-immiscible and can be found in the hydrocarbon, chlorinated hydrocarbon, ketone, ester, alcohol and amide classes of organic solvents. Mixtures of solvents are commonly employed. The surfactants useful as emulsifying agents can constitute about 0.5 to about 10% by weight of emulsifiable concentrates and can be anionic, cationic or non-ionic in character. The concentration of the active ingredients can vary from about 10 to about 80%, preferably in the range of about 25 to about 50%.
For use as pesticidal agents, these compounds should be applied in an effective amount sufficient to exert the desired pesticidal activity by techniques well known in the art. In certain situations, however, it may be desirable and advantageous to apply the compounds directly onto the loci to be protected or freed of pests without the benefit of any substantial amount of carrier. This is a particularly effective method when the physical nature of the toxicants is such as to permit what is known as "low-volume" application, that is, when the compounds are in liquid form or substantially soluble in higher boiling solvents.
The application rate will, of course, vary depending upon the purpose of such application, the compound being utilized, the frequency of dissemination, and the like.
Many of the above formulations can be utilized on animals for the control of parasites.
For use as arthropodicides, e.g. acaricides and insecticides, dilute sprays can be applied at concentrations of about 0.01 to about 20 pounds of the active ingredients per 100 gallons of spray. They are usually applied at about 0.1 to about 5 pounds per 100 gallons. In more concentrated sprays, the active ingredient is increased by a factor of 2 to 40. With dilute sprays, applications are usually made to the plants until run-off is achieved, whereas with more concentrated or low-volume sprays, the materials are applied as mists.
For use as a nematocide or as a soil insecticide, the compounds can be applied as a dilute liquid preparation or as a solid formulation, preferably a granular formulation, by broadcasting, side-dressing, introduction into the seed furrow, soil incorporation, or seed treatment. The application rate can be from about 1 to about 50 pounds per acre of active ingredient and for economic reasons, preferably from about 1 to about 25 pounds per acre.
For use as a fungicide, the organophosphorothiolate or phosphorodithioate can be applied by methods commonly employed, such as conventional high-gallonage hydraulic sprays, low-gallonage sprays, air-blast sprays, aerial sprays and dusts. The dilution and rate of application will depend upon the type of equipment employed, the method of application and diseases to be controlled, but the preferred effective amount is usually about 0.1 to about 50 pounds per acre of the active ingredient.
As a fungicidal seed protectant, the amount of toxicant coated on the seed is usually at a dosage rate of about 0.1 to about 20 ounces per hundred pounds of seed. As a soil fungicide the chemical can be incorporated in the soil or applied to the surface usually at a rate of about 0.1 to about 50 pounds per acre. As a foliar fungicide, the toxicant is usually applied to growing plants at a rate of about 0.25 to about 10 lbs. per acre.
The compounds of this invention can be utilized as the sole pesticidal agents or they can be employed in conjunction with other bactericides, fungicides, herbicides, insecticides, acaricides, and comparable pesticides.

The following examples are presented to illustrate but a few embodiments of the invention and are not to be constructed as limiting in scope. All parts and percentages are by weight unless otherwise indicated.
EXPERIMENTAL SECTION
Example 1: N-ethyl N-hydrocgencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioates
A solution of N-ethyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate, 120.5 g (0.50 mol), in 750 ml of dry tetrahydrofuran (THF) is cooled to (-) 78.degree. C. while being maintained under a nitrogen atmosphere. To this there is added a hexane solution, 229 ml, containing butyllithium (0.55 mol). The resulting reaction mixture is stirred for about 0.25 hr and to this there is then added all-at-once acetic-formic anhydride (0.55 mol). The resulting reaction mixture is then warmed to 0.degree. C. over period of 2 hrs and filtered through a celite filter pad. The solvent and excess acetic-formic anhydride and acetic acid by-product are removed from the filtrate by distillation under reduced pressure to afford 118.6 g (88% of theory) of product as a clear yellow oil.
Examples 2-6 are prepared by a procedure analogous to that of Example 1 except that acetic anhydride or trifluoroacetic anhydride are substituted for acetic-formic anhydride in several of these Examples:
Example 2: N-ethyl N-methylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 3: N-ethyl N-trifluoromethylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 4: N-ethyl N-hydrogencarbonyl O-ethyl s-methyl phosphoroamidodithioate
Example 5: N-ethyl N-hydrogencarbonyl O-ethyl S-(5-methyl-1,2,4-oxadiazolymethyl)phosphoroamidodithioate
Example 6: N-(2,2,2-trifluoroethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate.
Example 7: N-methyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithoate
Formic acid, 4.48 g (0.105 mol) and acetic anhydride, 7.96 g (0.078 mol) are mixed in a flask at room temperature and allowed to stand for 0.5 hr. After cooling this mixture in an ice bath, there is added N-methyl O-ethyl S-(1-methylpropyl phosphoroamidodithioate, 12 g (0.0527 mol). The resulting reaction mixture is warmed to room temperature and stirred for 1 day at room temperature. Removal of excess acetic-formic anhydride and acetic acid by-product from the resulting reaction mixture by distillation under reduced pressure affords 13.4 g (100% of theory) of product as a colorless oil.
Examples 8-15 and 49-65 are prepared by a procedure analogous to that of Example 7:
Example 8: N-methyl N-hydrogencarbonyl O-ethyl S-ethyl phosphoroamidodithioate
Example 9: N-methyl N-hydrogencarbonyl O-methyl S-(1-methylpropyl)phosphoroamidothioate
Example 10: N-methyl N-hydrogencarbonyl O-m-trifluoromethylphenyl S-(1-methylpropyl)phosphoroamidodithioate
Example 11: N-methyl N-hydrogencarbonyl O-ethyl S-propyl phosphoroamidodithioate
Example 12: N-methyl N-hydrogencarbonyl O-ethyl S-isopropyl phosphoroamidodithioate
Example 13: N-methyl N-hydrogencarbonyl O-ethyl S-tert-butyl phosphoroamidodithioate
Example 14: N-methyl N-hydrogencarbonyl O-ethyl S-(3-pentyl)phosphoroamidodithioate
Example 15: N-methyl N-hydrogencarbonyl O-ethyl S-allyl phosophoroamidodithioate
Example 16: N-ethyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
A solution of N-ethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate, 65 g (0.24 mol), and 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetan, 60.7 g (0.15 mol) in 750 ml of 1,2-dimethoxyethane is stirred and heated at reflux temperature for about 2 hr. The resulting clear yellow solution is cooled and the solvent is removed by distillation under reduced pressure. Hexane, 1L, is added to the residue and the resulting mixture is first stirred vigorously for 0.25 hr and then allowed to stand for 0.25 hr. The hexane layer is decanted-off and the hexane is removed from this portion by distillation under reduced pressure to afford 42 g (61% of theory) of product as a yellow oil. The product can be further purified by eluting a hexane solution of the product on a chromatographic column using Bio-Sil A.RTM. (a silica gel chromatography support product available from Biorad Laboratories).
Examples 17-26 and 66-94 are prepared by a procedure analogous to that of Example 16:
Example 17: N-methylthiomethyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 18: N-ethyl N-hydrogenthiocarbonyl O-ethyl S-methyl phosphoroamidodithioate
Example 19: N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-propyl phosphoroamidodithoate
Example 20: N-methyl N-hydrogenthiocarbonyl O-ethyl S-isopropyl phosphoroamidodithioate
Example 21: N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 22: N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 23: N-allyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoramidodithioate
Example 24: N-methyl N-hydrogenthiocarbonyl O-ethyl S-tert-butyl phosphoroamidodithioate
Example 25: N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-pentyl)phosphoroamidodithioate
Example 26: N-methyl N-hydrogenthiocarbonyl O-ethyl s-(1-methylpropyl)phosphoroamidothioate
In Examples 27-37 and 95-120, a phosphoroamidothioate precursor is substituted for a phosphoroamidodithioate precursor used in Example 16.
Example 27: N-propyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
Example 28: N-butyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
Example 29: N-benzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
Example 30: N-methylthiomethyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
Example 31: N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethyl phosphoroamidothioate
Example 32: N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-propyl phosphoroamidothioate
Example 33: N-methyl N-hydrogenthiocarbonyl O-ethyl S-isopropyl phosphoroamidothioate
Example 34: N-allyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
Example 35: N-methyl N-hydrogenthiocarobnyl O-ethyl S-(3-pentyl)phosphoroamidothioate
Example 36: N-ethyl N-hydrogenthiocarbonyl O-ethyl S-(3-pentyl)phosphoroamidothioate
Example 37: N-allyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
To a solution of N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate, 11.2 g (0.46 mol), and ally bromide, 9.4 g (0.056 mol), in 100 ml of methyl ethyl ketone is added powdered K.sub.2 CO.sub.3, 8.32 g (0.060 mol). The resulting suspension is stirred in ambient temperature for 24 hr. and then filtered. The solvent is removed from the filtrate by distillation under reduced pressure to afford 9.1 g (87% of theory) of product as a pale yellow oil. Further purification can be effected by high pressure liquid chromatography (HPLC) techniques.
Examples 38-41 and 121-146 are prepared by a procedure analogous to that of Example 37:
Example 38: N-propargyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 39: N-methylthiomethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 40: N-butyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate
Example 43: Preparation of ##STR9## N-Hydrogencarbonyl N-methyl S-(1-methylpropyl)S'-propyl phosphoroamidodithioate
STEP 1 ##STR10## Preparation of N-methyl S-(1-methylpropyl)S'-propyl phosphoroamidothioate
A solution of n-propyl mercaptan (23.63 g., 0,311 moles) and triethylamine (31.41 g., 0.311 moles) in 100 ml of tetrahydrofuran is added dropwise to an ice-cooled solution of S-(1-methylpropyl)phosphorodichloridothioate (64.4 g., 0.311 moles) in 200 ml of THF. The reaction was stirred 1 hr. at R.T., then methylamine (19.3 g., 0.622 moles) is bubbled into the reaction mixture. The reaction is diluted with ether, filtered through celite to remove the triethylamine hydrochloride and methylamine hydrochloride, and evaporated to give 75 grams of product as an oil which is purified by preparative high pressure liquid chromatography (HPLC), using two prepPak 500 silica gel columns in series.
STEP 2 ##STR11##
Formic acid, 97%, (1.04 g., 0.026 moles) is added to acetic anhydride (2.10 g., 0.0206 moles) and stirred 15 min. at room temperature. The resulting formic-acetic anhydride is added to N-methyl S-(1-methylpropyl)S'-(propyl)phosphoramidodithioate (2.5 g., 0.0103 mole) and three drops of 85% phosphoric acid. The reaction is stirred 24 hours at room temperature and evaporated under high vacuum to remove acetic acid and formic-acetic anhydride, leaving 2.1 g. of material. Purification by preparative HPLC gave 0.5 of product as an oil.
Example 147: N-methylthiomethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate
To a solution of N-hydrogencarbonyl O-ethyl S-(1-methyl-propyl)phosphoroamidothioate, 4.0 g (0.018 mol) and chloromethyl methyl sulfide, 1.84 g (0.019 mol) in 100 ml of methyl ethyl ketone is added powdered K.sub.2 CO.sub.3, 3.73 g (0.027 mol). The resulting suspension is stirred in ambient temperature for 24 hr. and then filtered. The solvent is removed from the filtrate by distillation under reduced pressure to afford 4.3 g (84% of theory) of product as a pale yellow oil. Further purification can be effected by high pressure liquid chromatography (HPLC) techniques.
Examples 148-179 are prepared by a procedure analogous to that of Example 147.
Table I below depicts the various substituent groups in the illustrative compounds made according to formula (I) above:
TABLE I__________________________________________________________________________Tabular List of Substituents in Examples ##STR12##Example X Y Z R.sup.1 R.sup.2 R.sup.3 R.sup.4__________________________________________________________________________1 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H C.sub.2 H.sub.52 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 CH.sub.3 C.sub.2 H.sub.53 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 CF.sub.3 C.sub.2 H.sub.54 S O O C.sub.2 H.sub.5 CH.sub.3 H C.sub.2 H.sub.55 S O O C.sub.2 H.sub.5 ##STR13## H C.sub.2 H.sub.56 S O O C.sub. 2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CF.sub.37 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.38 S O O C.sub.2 H.sub.5 C.sub.2 H.sub.5 H CH.sub.39 S O O CH.sub.3 .sub.-s-C.sub.4 H.sub.9 H CH.sub.310 S O O .sub.--m-CF.sub.3C.sub.6 H.sub.4 .sub.-s-C.sub.4 H.sub.9 H CH.sub.311 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.312 S O O C.sub.2 H.sub.5 .sub.-i-C.sub.3 H.sub.7 H CH.sub.313 S O O C.sub.2 H.sub.5 .sub.-t-C.sub.4 H.sub.9 H CH.sub.314 S O O C.sub.2 H.sub.5 CH(C.sub.2 H.sub.5).sub.2 H CH.sub.315 S O O C.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2 H CH.sub.316 S S O C.sub.2 H.sub.5 .sub.- s-C.sub.4 H.sub.9 H C.sub.2 H.sub.517 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SCH.sub.318 S S O C.sub.2 H.sub.5 CH.sub.3 H C.sub.2 H.sub.519 S S O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.320 S S O C.sub.2 H.sub.5 .sub.-i-C.sub.3 H.sub.7 H CH.sub.321 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H H22 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.323 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCH.sub.224 S S O C.sub.2 H.sub.5 .sub.-t-C.sub.4 H.sub.9 H CH.sub.325 S S O C.sub.2 H.sub.5 CH(C.sub.2 H.sub.5).sub.2 H CH.sub.326 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub. 9 H CH.sub.327 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H -n-C.sub.3 H.sub.728 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H -n-C.sub.4 H.sub.929 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.530 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SCH.sub.331 O S O C.sub.2 H.sub.5 C.sub.2 H.sub.5 H CH.sub.332 O S O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.333 O S O C.sub.2 H.sub.5 .sub.-i-C.sub.3 H.sub.7 H CH.sub.334 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCH.sub.235 O S O C.sub.2 H.sub.5 CH(C.sub.2 H.sub.5).sub.2 H CH.sub.336 O S O C.sub.2 H.sub.5 CH(C.sub.2 H.sub.5).sub.2 H C.sub.2 H.sub.537 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCH.sub.238 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCH39 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SCH.sub.340 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H -n-C.sub.4 H.sub.941 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H H42 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CN43 O O S -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.9 H CH.sub.344 O O S .sub.-s-C.sub.4 H.sub.9 .sub.-s-C.sub. 4 H.sub.9 H CH.sub.345 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H H46 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CN47 O S O -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.3 H CH.sub.348 O S O .sub.-s-C.sub.4 H.sub.9 .sub.-s-C.sub.4 H.sub.9 H CH.sub.349 S O O C.sub.2 H.sub.5 .sub.-i-C.sub.4 H.sub.9 H CH.sub.350 S O O C.sub.2 H.sub.5 -n-C.sub.4 H.sub.9 H CH.sub.351 S O O C.sub.2 H.sub.5 .sub.-i-C.sub.5 H.sub.11 H CH.sub.352 S O O C.sub.2 H.sub.5 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.353 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.5 H.sub.11 H CH.sub.354 S O O C.sub.2 H.sub. 5 CH.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.355 S O O C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.356 S O O CH.sub.2 CF.sub.3 .sub.-s-C.sub.4 H.sub.9 H CH.sub.357 S O O C.sub.2 H.sub.5 CH(C.sub.2 H.sub.5).sub.2 H CH.sub.358 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H C.sub.2 H.sub.559 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H H60 S O O -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.9 H C.sub.2 H.sub.561 S O O -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.9 H CH.sub.362 S O O CH.sub.2 CF.sub.3 .sub.-s-C.sub.4 H.sub.9 H C.sub.2 H.sub.563 S O O CH.sub.2 CH.sub.2 F .sub.-s-C.sub.4 H.sub.9 H CH.sub.364 S O O CH.sub.2 CH.sub.2 OCH.sub.3 .sub.-s-C.sub.4 H.sub.9 H CH.sub.365 S O O CH.sub.2 CF.sub.2 CF.sub.2 H .sub.-s-C.sub.4 H.sub.9 H CH.sub.366 S S O 3-CF.sub.3 C.sub.6 H.sub.4 .sub.-s-C.sub.4 H.sub.9 H CH.sub.367 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SCH.sub.368 S S O C.sub.2 H.sub.5 .sub.-i-C.sub.4 H.sub.9 H CH.sub.369 S S O C.sub.2 H.sub.5 -n-C.sub.4 H.sub.9 H CH.sub.370 S S O C.sub.2 H.sub.5 .sub.-i-C.sub.5 H.sub.11 H CH.sub.371 S S O C.sub.2 H.sub.5 -n-C.sub.5 H.sub.11 H CH.sub.372 S S O C.sub.2 H.sub.5 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.373 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.5 H.sub.11 H CH.sub.374 S S O C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.375 S S O C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.376 S S O CH.sub.2 CF.sub.3 .sub.-s-C.sub.4 H.sub.9 H CH.sub.377 S S O -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.9 H C.sub.2 H.sub.578 S S O -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.9 H CH.sub.379 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CO.sub.2 CH.sub.380 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.581 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 F482 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 OCH.sub.3383 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CF.sub.3384 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CH.sub.2 CH.sub.2 Cl85 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SC.sub.6 H.sub.4 Cl486 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C(Br)CH.sub.287 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCHC.sub.6 H.sub.588 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CO.sub.2 C.sub.2 H.sub.589 S S O C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.390 S S O CH.sub.2 CF.sub.2 CF.sub.2 H .sub.-s-C.sub.4 H.sub.9 H CH.sub. 391 S S O CH.sub.2 CF.sub.3 .sub.-s-C.sub.4 H.sub.9 H C.sub.2 H.sub.592 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SC.sub.6 H.sub.593 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCHCH.sub.394 S S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 NO.sub.2495 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CCH96 O S O CH.sub.2 CF.sub.3 .sub.-s-C.sub.4 H.sub.9 H CH.sub.397 O S O C.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2 H CH.sub.398 O S O C.sub.2 H.sub.5 s-C.sub.4 H.sub.9 H CH.sub.399 O S O C.sub.2 H.sub.5 -n-C.sub.4 H.sub.9 H CH.sub.3100 O S O C.sub.2 H.sub.5 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3101 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.5 H.sub.11 H CH.sub.3102 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H C.sub.2 H.sub.5103 O S O -n-C.sub.3 H.sub.7 .sub.-s-C.sub.4 H.sub.9 H CH.sub.3104 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 F4105 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33106 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CF.sub.33107 O S O CH.sub.2 CH.sub.2 F .sub.-s-C.sub.4 H.sub.9 H CH.sub.3108 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub. 9 H CH.sub.2 CHCHCH.sub.3109 O S O C.sub.2 H.sub.5 C.sub.3 H.sub.7 H CH.sub.2 CHCH.sub.2110 O S O C.sub.2 H.sub.5 C.sub.3 H.sub.7 H CH.sub.2 CCH111 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.10 H.sub.7112 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 Br2113 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 ClF2,6113 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 ClF2,6114 O S O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H -n-C.sub.3 H.sub.7115 O S O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H -n-C.sub. 4 H.sub.9116 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 CH.sub.3 NO.sub.23,4117 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 F.sub.52,3,4,5,6118 O S O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 Cl.sub.22,6119 O S O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 C.sub.6 H.sub.5120 O S O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 CO.sub.2 CH.sub.3121 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CO.sub.2 CH.sub.3122 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.5123 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 F4124 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33125 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CF.sub.33126 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CH.sub.2 CH.sub.2 Cl127 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SC.sub.6 H.sub.4 Cl4128 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C(Br)CH.sub.2129 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCHC.sub.6 H.sub.5130 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CO.sub.2 C.sub.2 H.sub.5131 S O O C.sub.2 H.sub.5 -n-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 NO.sub.24132 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CN4133 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C(O)C.sub.6 H.sub.5134 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 Br2135 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 OC.sub.6 H.sub.4 Cl4136 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.10 H.sub.7137 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCHCH.sub.3138 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 ClF2,6139 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub. 9 H CH.sub.2 C.sub.6 F.sub.52,3,4,5,6140 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H -n-C.sub.4 H.sub.9141 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 C.sub.6 H.sub.5142 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 CO.sub.2 C.sub.2 H.sub.5143 S O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 CH.sub.2 CH.sub.2 Cl144 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5145 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H ##STR14##146 S O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C(CH.sub.3)CH.sub.2147 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SCH.sub.3148 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.5149 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CN150 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 OCH.sub.3151 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CH.sub.2 CH.sub.2 Cl152 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 F4153 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33154 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CF.sub.33155 O O O C.sub.2 H.sub. 5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SC.sub.6 H.sub.4 Cl4156 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CHCHC.sub.6 H.sub.5157 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 SC.sub.6 H.sub.5158 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CH.sub.32159 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 NO.sub.24160 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 CH.sub.2 CH.sub.2 Cl161 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C(O)C.sub.6 H.sub.5162 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.10 H.sub.7163 O O O C.sub. 2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 Br2164 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.2 H.sub.3 ClF2,6165 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 F.sub.52,3,4,5,6166 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 Cl.sub.22,6167 O O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 C.sub.6 H.sub.5168 O O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 C.sub.6 H.sub.4 F4169 O O O C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 H CH.sub.2 C.sub.6 H.sub.3 ClF2,6170 O O O CH.sub.2 CH.sub.2 F .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.5171 O O O CH.sub.2 CH.sub.2 F .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 NO.sub.24172 O O O C.sub.2 H.sub.5 -n-C.sub.3 H.sub.7 H CH.sub.2 C.sub.6 H.sub.4 CF.sub.33173 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H(CH.sub.3).sub.42,3,5, 6174 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 C(O)CH.sub.33175 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CH.sub.32176 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 CH.sub.3 NO.sub.23,4177 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 F3178 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub. 9 H CH.sub.2 C.sub.6 H.sub.3 Cl.sub.23,4179 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.3 (CH.sub.3).sub. 22,5180 O O O C.sub.2 H.sub.5 .sub.-s-C.sub.4 H.sub.9 H CH.sub.2 C.sub.6 H.sub.4 CN4__________________________________________________________________________
Tables II and III which follow, respectively, set forth the analytical data and nuclear magnetic resonance (nmr) data of representative compounds selected from Table I.
TABLE II______________________________________Elemental AnalysisEx- % Calcd. (Found)ample Emp. Formula C H N______________________________________ 1 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.10(39.21) 7.50(7.54) 5.20(4.66) 2 NA 3 C.sub.10 H.sub.19 F.sub.3 NO.sub.2 PS.sub.2 35.59(36.30) 5.68(5.40) 4.15(4.13) 4 C.sub.6 H.sub.14 NOPS.sub.2 34.10(33.99) 6.68(6.23) 6.63(6.29) 5 NA 6 NA 7 C.sub.8 H.sub.18 NO.sub.2 PS.sub.2 37.60(38.10) 7.10(7.05) 5.48(5.49) 8 C.sub.6 H.sub.14 NO.sub.2 PS.sub.2 31.71(31.41) 6.21(6.43) 6.16(6.16) 9 C.sub.7 H.sub.16 NO.sub.2 PS.sub.2 34.83(35.13) 6.68(6.97) 5.80(5.56) 10 NA 11 C.sub.7 H.sub.16 NO.sub.2 PS.sub.2 34.83(34.39) 6.68(6.34) 5.80(6.12) 12 C.sub.7 H.sub.16 NO.sub.2 PS.sub.2 34.84(34.97) 6.68(6.80) 5.80(5.65) 13 C.sub.8 H.sub.18 NO.sub.2 PS.sub.2 37.62(36.81) 7.10(7.02) 5.48(6.19) 14 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.13(41.04) 7.48(7.64) 5.20(5.09) 15 NA 16 C.sub.9 H.sub.20 NOPS.sub.3 37.87(39.58) 7.06(7.38) 4.91(4.99) 17 NA 18 C.sub.9 H.sub.20 NOPS.sub.4 34.00(35.74) 6.34(6.65) 4.41(3.78) 19 NA 20 NA 21 C.sub.6 H.sub.14 NOPS.sub.3 29.61(30.48) 5.80(5.76) 5.76(5.88) 22 C.sub.7 H.sub.16 NOPS.sub.3 32.66(33.61) 6.27(7.06) 5.44(6.57) 23 C.sub.7 H.sub.16 NOPS.sub.3 32.66(32.48) 6.27(6.09) 5.44(5.28) 24 C.sub.7 H.sub.16 NOPS.sub.3 32.66(33.14) 6.26(6.42) 5.44(5.65) 25 C.sub.8 H.sub.18 NOPS.sub.3 35.40(36.16) 6.68(6.93) 5.16(5.36) 26 C.sub.10 H.sub.20 NOPS.sub.3 40.37(40.46) 6.77(7.24) 4.70(5.12) 27 C.sub.8 H.sub.18 NOPS.sub.3 35.40(35.75) 6.68(6.85) 5.16(5.35) 28 C.sub.9 H.sub.20 NOPS.sub.3 37.87(38.73) 7.06(7.17) 4.91(5.26) 29 C.sub.8 H.sub.18 NO.sub.2 PS.sub.2 37.62(36.06) 7.10(7.09) 5.48(5.58) 30 C.sub.10 H.sub.22 NO.sub.2 PS.sub.2 42.30(42.20) 7.82(7.91) 4.94(4.88) 31 C.sub.11 H.sub.24 NO.sub.2 PS.sub.2 44.40(44.20) 8.13(8.16) 4.70(4.72) 32 C.sub.14 H.sub.22 NO.sub.2 PS.sub.2 50.73(49.74) 6.69(6.73) 4.22(4.29) 33 C.sub.9 H.sub.20 NO.sub.2 PS.sub.3 35.85(35.85) 6.68(6.53) 4.64(4.77) 34 C.sub.6 H.sub.14 NO.sub.2 PS.sub.2 31.70(31.14) 6.21(6.95) 6.16(6.35) 35 C.sub.7 H.sub.16 NO.sub.2 PS.sub.2 34.83(34.24) 6.68(6.71) 5.80(5.78) 36 C.sub.7 H.sub.16 NO.sub.2 PS.sub.2 34.84(34.38) 6.68(6.88) 5.80(5.91) 37 C.sub.10 H.sub.20 NO.sub.2 PS.sub.2 42.68(41.74) 7.16(7.22) 4.97(5.12) 38 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.13(39.96) 7.48(7.65) 5.20(5.35) 39 C.sub.10 H.sub.22 NO.sub.2 PS.sub.2 42.65(42.28) 8.29(7.94) 5.24(5.29) 40 C.sub.10 H.sub.20 NO.sub.2 PS.sub.2 42.68(42.71) 7.16(7.31) 4.97(5.15) 41 C.sub.10 H.sub.18 NO.sub.2 PS.sub.3 42.99(42.41) 6.49(6.23) 5.01(5.34) 42 C.sub.9 H.sub.20 NO.sub.2 PS.sub.3 35.85(35.98) 6.68(6.55) 4.64(4.76) 43 NA 44 C.sub.11 H.sub.24 NO.sub.2 PS.sub.2 44.41(44.07) 8.13(8.12) 4.70(4.79) 45 C.sub.7 H.sub.16 NO.sub.2 PS.sub.2 34.8(35.16) 6.70(6.83) 5.80(4.87) 46 C.sub.9 H.sub.17 N.sub.2 O.sub.2 PS.sub.2 38.55(38.07) 6.11(6.16) 9.99(9.61) 47 48 49 C.sub.8 H.sub.18 NO.sub.2 PS.sub.2 37.62(37.64) 7.10(6.99) 5.48(5.36) 50 C.sub.8 H.sub.18 NO.sub.2 PS.sub.2 37.62(37.53) 7.10(6.99) 5.48(5.56) 51 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.12(39.88) 7.48(7.54) 5.20(5.28) 52 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.12(40.32) 7.48(7.58) 5.20(5.42) 53 C.sub.8 H.sub.16 NO.sub.2 PS.sub.2 37.92(38.42) 6.36(6.55) 5.52(5.67) 54 C.sub.8 H.sub.16 NO.sub.2 PS.sub.2 37.92(38.42) 6.36(6.55) 5.52(5.67) 55 C.sub.7 H.sub.16 NO.sub.3 PS.sub.2 32.67(31.96) 6.26(6.19) 5.44(4.99) 56 NA 57 NA 58 NA 59 NA 60 NA 61 NA 62 NA 63 C.sub.8 H.sub.17 FNO.sub.2 PS.sub.2 35.15(35.67) 6.27(5.98) 5.12(4.69) 64 C.sub.9 H.sub.20 NO.sub.3 PS.sub.2 37.88(37.73) 7.06(7.16) 4.91(4.73) 65 C.sub.9 H.sub.16 F.sub.4 NO.sub.2 PS.sub.2 31.67(32.18) 4.73(4.70) 4.10(3.29) 66 C.sub.13 H.sub.17 F.sub.3 NOPS.sub.3 40.29(41.98) 4.42(5.24) 3.62(3.72) 67 C.sub.9 H.sub.20 NOPS.sub.4 34.40(35.74) 6.34(6.65) 4.41(3.55) 68 C.sub.8 H.sub.18 NOPS.sub.3 35.40(35.49) 6.68(6.54) 5.16(5.02) 69 C.sub.8 H.sub.18 NOPS.sub.3 35.40(35.96) 6.68(6.70) 5.16(5.21) 70 C.sub.9 H.sub.20 NOPS.sub.3 37.86(39.03) 7.06(7.48) 4.90(4.94) 71 C.sub.9 H.sub.22 NOPS.sub.3 37.86(38.84) 7.06(7.42) 4.90(5.13) 72 C.sub.9 H.sub.20 NOPS.sub.3 37.86(39.48) 7.06(7.42) 4.90(4.80) 73 C.sub.9 H.sub.20 NOPS.sub.3 37.86(39.26) 7.06(7.62) 4.9(4.95) 74 C.sub.8 H.sub.16 NOPS.sub.3 35.66(37.50) 5.98(6.57) 5.19(6.57) 75 C.sub.7 H.sub.16 NO.sub.1 PS.sub.3 30.75(31.79) 5.90(6.20) 5.12(4.65) 76 NA 77 NA 78 NA 79 C.sub.10 H.sub.20 NO.sub.3 PS.sub.3 36.45(37.01) 6.11(6.31) 4.25(4.57) 80 C.sub.14 H.sub.22 NOPS.sub.3 48.38(50.57) 6.38(6.44) 4.03(3.82) 81 C.sub.14 H.sub.21 FNOPS.sub.3 46.0(45.73) 5.79(5.67) 3.83(3.70) 82 C.sub.15 H.sub.24 NO.sub.2 PS.sub.3 47.71(47.97) 6.40(6.65) 3.71(3.69) 83 C.sub.15 H.sub.21 F.sub.3 NOPS.sub.3 43.35(44.76) 5.09(5.12) 3.37(3.13) 84 C.sub.10 H.sub.21 CLNOPS.sub.3 35.96(36.60) 6.34(6.60) 4.19(3.74) 85 C.sub.14 H.sub.21 CLNOPS.sub.4 40.6(43.04) 5.10(5.20) 3.38(2.82) 86 C.sub.10 H.sub.19 BrNOPS.sub.3 31.91(32.67) 5.08(5.34) 3.72(3.33) 87 C.sub.16 H.sub.24 NOPS.sub.3 51.4(51.18) 6.47(6.60) 3.75(3.99) 88 C.sub.11 H.sub.22 NO.sub.3 PS.sub.3 38.46(38.85) 6.45(6.68) 4.07(4.22) 89 C.sub.11 H.sub.24 NO.sub.2 PS.sub.3 40.09(38.79) 7.34(6.71) 4.25(4.11) 90 NA 91 NA 92 NA 93 NA 94 95 C.sub.10 H.sub.18 NO.sub.2 PS.sub.2 42.99(40.58) 6.49(6.86) 5.01(4.81) 96 C.sub.8 H.sub.15 F.sub.3 NO.sub.2 PS.sub.2 31.06(31.69) 4.89(4.80) 4.52(4.60) 97 C.sub.7 H.sub.14 NO.sub.2 PS.sub.2 35.13(35.10) 5.89(6.03) 5.85(5.97) 98 C.sub.8 H.sub.18 NO.sub.2 PS.sub.2 37.62(37.80) 7.10(7.12) 5.48(5.72) 99 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.10(39.58) 7.48(7.55) 5.20(5.01)100 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.10(39.60) 7.48(7.67) 5.20(5.18)101 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.10(38.83) 7.48(7.48) 5.20(4.87)102 NA103 NA104 C.sub.14 H.sub.21 FNO.sub.2 PS.sub.2 48.11(48.01) 6.05(6.10) 4.00(4.04)105 C.sub.15 H.sub.24 NO.sub.3 PS.sub.2 49.84(49.59) 6.69(6.44) 3.87(4.23)106 C.sub.15 H.sub.21 F.sub.3 NO.sub.2 PS.sub.2 45.10(45.18) 5.30(5.48) 3.50(3.44)107 NA108 C.sub.11 H.sub.22 NO.sub.2 PS.sub.2 44.72(44.52) 7.50(7.65) 4.74(4.90)109 C.sub.9 H.sub.18 NO.sub.2 PS.sub.2 40.4(37.86) 6.78(6.91) 5.23(6.13)110 C.sub.9 H.sub.16 NO.sub.2 PS.sub.2 40.73(40.49) 6.07(6.32) 5.27(5.35)111 C.sub.18 H.sub.24 NO.sub.2 PS.sub.2 56.66(55.68) 6.34(6.49) 3.67(3.42)112 C.sub.14 H.sub.21 BrNO.sub.2 PS.sub.2 40.97(41.43) 5.15(5.12) 3.41(3.42)113 C.sub.14 H.sub.20 ClFNO.sub.2 PS.sub.2 43.80(44.35) 5.25(4.68) 3.64(2.33)114 C.sub.9 H.sub.20 NO.sub.2 PS.sub.2 40.12(40.45) 7.48(6.74) 5.20(4.16)115 C.sub.10 H.sub.22 NO.sub.2 PS.sub.2 42.37(41.58) 7.82(7.66) 4.94(4.82)116 C.sub.15 H.sub.23 N.sub.2 O.sub.5 PS.sub.2 48.11(47.80) 6.19(6.52) 7.48(7.33)117 C.sub.14 H.sub.17 F.sub.5 NO.sub.2 PS.sub.2 39.90(40.14) 4.06(4.16) 3.32(3.60)118 C.sub.14 H.sub.20 Cl.sub.2 NO.sub.2 PS.sub.2 42.00(41.93) 5.03(4.88) 3.49(2.77)119 NA120 NA121 C.sub.10 H.sub.20 NO.sub.4 PS.sub.2 38.32(38.48) 6.43(6.60) 4.47(4.88)122 C.sub.14 H.sub.22 NO.sub.2 PS.sub.2 50.73(52.49) 6.69(6.86) 4.22(3.95)123 C.sub.14 H.sub.21 FNO.sub.2 PS.sub.2 48.11(46.97) 6.00(6.02) 4.00(3.76)124 C.sub.15 H.sub.24 NO.sub.3 PS.sub.2 49.84(49.17) 6.69(6.71) 3.87(3.72)125 C.sub.15 H.sub.21 F.sub.3 NO.sub.2 PS.sub.2 45.10(45.60) 5.30(5.45) 3.50(3.72)126 C.sub.10 H.sub.21 ClNO.sub.2 PS.sub.2 37.78(36.90) 6.66(6.74) 4.40(4.65)127 C.sub.14 H.sub.21 ClNO.sub.2 PS.sub.2 42.25(42.01) 5.31(5.49) 3.52(3.80)128 C.sub.10 H.sub.19 BrNO.sub.2 PS.sub.2 33.30(33.93) 5.31(5.41) 22.18(20.64)129 C.sub.16 H.sub.24 NO.sub.2 PS.sub.2 53.75(53.71) 6.70(6.72) 3.91(3.96)130 C.sub.11 H.sub.22 NO.sub.4 PS.sub.2 40.35(40.31) 6.77(6.87) 4.27(4.67)131 C.sub.14 H.sub.21 N.sub.2 O.sub.4 PS.sub.2 44.60(43.52) 5.62(5.74) 7.44(7.21)132 C.sub.15 H.sub.21 N.sub.2 O.sub.2 PS.sub.2 50.50(50.59) 5.93(6.08) 7.86(7.74)133 C.sub.15 H.sub.22 NO.sub.3 PS.sub.2 50.10(47.67) 6.17(6.49) 3.89(4.11)134 C.sub.14 H.sub.21 BrNO.sub.2 PS.sub.2 40.97(40.86) 5.15(5.01) 3.41(2.98)135 C.sub.14 H.sub.21 ClNO.sub.3 PS.sub.2 44.02(43.64) 5.54(5.55) 3.66(3.60)136 C.sub.18 H.sub.24 NO.sub.2 PS.sub.2 56.60(55.96) 6.34(6.13) 3.67(3.47)137 C.sub.11 H.sub.22 NO.sub.2 PS.sub.2 44.72(44.25) 7.50(7.71) 4.74(4.62)138 C.sub.14 H.sub.20 ClFNO.sub.2 PS.sub.2 43.80(43.63) 5.25(5.29) 3.64(3.47)139 C.sub.14 H.sub.17 F.sub.5 NO.sub.2 PS.sub.2 39.90(39.99) 4.06(4.13) 3.32(3.45)140 C.sub.10 H.sub.22 NO.sub.2 PS.sub.2 42.37(42.10) 7.82(7.58) 4.94(5.30)141 C.sub.13 H.sub.20 NO.sub.2 PS.sub.2 49.18(49.13) 6.35(6.34) 4.41(4.79)142 C.sub.10 H.sub.20 NO.sub.4 PS.sub.2 38.30(38.21) 6.43(6.53) 4.46(4.76)143 C.sub.9 H.sub.19 ClNO.sub.2 PS.sub.2 35.57(35.34) 6.30(6.36) 4.61(4.81)144 C.sub.21 H.sub.28 NO.sub.3 PS.sub.2 57.64(55.83) 6.44(6.43) 3.20(3.49)145 C.sub.15 H.sub.21 ClNO.sub.4 PS.sub.2 43.95(43.74) 5.16(5.22) 3.41(3.48)146 C.sub.11 H.sub.22 NO.sub.2 PS.sub.2 44.72(44.55) 7.50(7.46) 4.74(4.62)147 C.sub.9 H.sub.20 NO.sub.3 PS.sub.2 37.8(38.09) 7.10(7.36) 4.6(5.45)148 C.sub.14 H.sub.22 NO.sub.3 PS 53.3(54.74) 7.00(7.23) 4.4(5.20)149 C.sub.9 H.sub.17 N.sub.2 O.sub.3 PS 40.89(41.03) 6.48(6.74) 10.60(10.05)150 C.sub.9 H.sub.20 NO.sub.4 PS 40.10(40.71) 7.48(8.00) 5.20(4.68)151 C.sub.10 H.sub.21 ClNO.sub.3 PS 39.79(38.14) 7.00(7.00) 4.64(4.58)152 C.sub.14 H.sub.21 FNO.sub.3 PS 50.43(50.64) 6.35(6.44) 4.20(4.21)153 C.sub.15 H.sub.24 NO.sub.4 PS 52.15(51.79) 7.00(7.04) 4.05(4.38)154 C.sub.15 H.sub.21 F.sub.3 NO.sub.3 PS 46.99(47.57) 5.52(5.69) 3.65(3.60)155 C.sub.14 H.sub.21 ClNO.sub.3 PS.sub.2 44.00(43.80) 5.54(572) 3.66(3.81)156 C.sub.16 H.sub.24 NO.sub.3 PS 56.28(55.80) 7.08(7.08) 4.10(3.92)157 C.sub.14 H.sub.22 NO.sub.3 PS 48.39(48.54) 6.38(6.57) 4.03(4.11)158 C.sub.15 H.sub.24 NO.sub.3 PS 54.69(54.01) 7.34(7.56) 4.25(4.29)159 C.sub.14 H.sub.21 N.sub.2 O.sub.5 PS 46.65(46.33) 5.83(6.11) 7.77(7.56)160 C.sub.9 H.sub.19 ClNO.sub.3 PS 37.56(36.96) 6.65(6.80) 4.86(4.75)161 C.sub.15 H.sub.22 NO.sub.4 PS 52.46(51.71) 6.45(6.83) 4.07(4.29)162 C.sub.18 H.sub.24 NO.sub.3 PS 59.15(59.26) 6.61(6.79) 3.83(3L85)163 C.sub.14 H.sub.21 BrNO.sub.3 PS 42.64(42.89) 5.36(5.48) 3.55(3.44)164 C.sub.14 H.sub.20 ClFNO.sub.3 PS 45.71(45.60) 5.48(5.66) 3.80(3.91)165 C.sub.14 H.sub.17 F.sub.5 NO.sub.3 PA 41.48(41.54) 4.22(3.95) 3.45(3.66)166 C.sub.14 H.sub.10 Cl.sub.2 NO.sub.3 PS 43.75(43.47) 5.24(5.31) 3.64(3.88)167 C.sub.13 H.sub.20 NO.sub.3 PS 51.8(52.25) 6.69(6.59) 4.64(4.76)168 C.sub.13 H.sub.19 FNO.sub.3 PS 48.89(48.56) 5.99(6.05) 4.38(4.66)169 C.sub.13 H.sub.18 ClFNO.sub.3 PS 44.10(43.84) 5.12(5.32) 3.95(4.03)170 C.sub.14 H.sub.21 FNO.sub.3 PS 50.44(49.90) 6.35(6.61) 4.20(4.83)171 C.sub.14 H.sub.20 FN.sub.2 O.sub.5 PS 50.78(49.03) 5.33(5.31) 7.40(7.34)172 C.sub.14 H.sub.19 F.sub.3 NO.sub.3 PS 45.52(45.52) 5.18(5.11) 3.79(3.84)173 C.sub.18 H.sub.18 NO.sub.2 PS 19.64(50.10) 6.94(6.80) 3.21(3.45)174 C.sub.16 H.sub.24 NO.sub.4 PS 53.76(52.53) 6.76(6.56) 3.91(3.82)175 C.sub.15 H.sub.24 NO.sub.3 PS 54.69(54.68) 7.34(7.29) 4.25(4.16)176 C.sub.15 H.sub.23 N.sub.2 O.sub.5 PS 48.11(47.80) 6.19(6.52) 7.48(7.33)177 NA178 C.sub.14 H.sub.20 Cl.sub.2 NO.sub.3 PS 43.75(43.74) 5.24(5.27) 3.64(3.56)179 NA180 C.sub.15 H.sub.21 N.sub.2 O.sub.3 PS 52.92(52.20) 6.21(6.54) 8.23(8.11)______________________________________
TABLE III______________________________________Nuclear Magnetic Resonance Data (ppm, .delta.)______________________________________Example 1: 8.90(s, 1H, CCH); 4.30(m, 2H, OCH.sub.2 CH.sub.3); 3.68(m,1H,SCH) 3.60(m, 2H, NCH.sub.2); 1.64(m, 2H, SCHCH.sub.2); 1.40(m, 3H,SCH(CH.sub.3); 1.40 (t, 3H, OCH.sub.2 CH.sub.3); 1.40(t, 3H, NCH.sub.2CH.sub.3);1.20(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 2: 4.20(m, 2H, OCH.sub.2); 3.80(m, 2H, NCH.sub.2), 3.40(m, 1H,SCH), 2.20(s, 3H, NCOCH.sub.3); 1.64(m, 2H, SCHCH.sub.2); 1.40(t, 3H,OCH.sub.2 CH.sub.3); 1.40 (t, 3H, NCH.sub.2 CH.sub.3); 1.40(m, 3H,SCHCH.sub.3);1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 3: 4.30(m, 2H, OCH.sub.2); 3.80(m, 2H, NCH.sub.2), 3.40(m, 1H,SCH); 1.64(m, 2H, SCHCH.sub.2); 1.40(t, 3H, OCH.sub.2 CH.sub.3); 1.40(t,3H,NCH.sub.2 CH.sub.3); 1.40 (3H, SCHCH.sub.3); 1.00(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 4: 8.88(s, 1H, OCH); 4.38(m, 2H, OCH.sub.2); 3.70(m, 2H,NCH.sub.2); 2.41(d, 3H, SCH.sub.3); 1.40(q, 6H, NCH.sub.2 CH.sub.3 andOCH.sub.2 CH.sub.3)Example 5: 8.90(s, 1H, OCH); 4.38(m, 2H, OCH.sub.2); 4.30(d, 2H,SCH.sub.2); 3.58(m, 2H, NCH.sub.2); 2.58(s, 3H, ring CH.sub.3); 1.38(m,6H,NCH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.3)Example 6: 8.75(s, 1H, OCH); 4.40(m, 4H, OCH.sub.2 and NCH.sub.2);3.58(m, 1H, SCH); 1.84(m, 2H, SCHCH.sub.2); 1.50(m, D6H, OCH.sub.2CH.sub.3and SCHCH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 7: 8.90(s, 1H, OCH); 4.30(m, 2H, OCH.sub.2); 3.48(m, 1H,SCH); 308(d, 3H, NCH.sub.3)D; 1.78(m, 2H, SCHCH.sub.2); 1.38(t, 6H,OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.08(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 8: 8.92(s, 1H, OCH); 4.38(m, 2H, OCH.sub.2); 3.15(m, 2H,SCH.sub.2) 3.08(d, 3H, NCH.sub.3); 1.38(dt, 6H, SCH.sub.2 CH.sub.3 andOCH.sub.2 CH.sub.3)Example 9: 8.90(s, 1H, OCH); 3.80(d, 3H, OCH.sub.3); 3.40(m, 1H, SCH),3.00(d, 3H, NCH.sub.3); 1.70(m, 2H, SCHCH.sub.2); 1.40(t, 6H, OCH.sub.2CH.sub.3and SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 10: 8.85(s, 1H, OCH); 7.50(s, 4H, aromatic); 3.50(m, 1H,SCH); 3.19(d, 3H, NCH.sub.3); 1.70(m, 2H, SCHCH.sub.2); 1.38(d, 3H,SCHCH.sub.3); 0.98 (m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 11: 8.90(s, 1H, OCH); 4.30(m, 2H, OCH.sub.2); 3.00(d, 3H,NCH.sub.3); 2.80(m, 2H, SCH.sub.2); 1.78(m, 2H, SCH.sub.2 CH.sub.2);1.40(t, 3H,OCH.sub.2 CH.sub.3); 1.00 (t, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)Example 12: 8.88(s, 1H, OCH); 4.25(m, 2H, OCH.sub.2); 3.50(m, 1H,SC.sub.--H), 3.02(d, 3H, NCH.sub.3); 1.20(m, 9H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3).sub.2Example 13: 8.90(s, 1H, OCH); 4.20(m, 2H, OCH.sub.2); 2.98(d, 3H,NCH.sub.3); 1.58(d, 9H, SCH(CH.sub.3).sub.3 ; 1.30(t, 3H, OCH.sub.2CH.sub.3)Example 14: 8.90(s, 1H, OCH); 4.30(m, 2H, OCH.sub.2); 3.42(m, 1H,SCH); 1.78(m, 4H, SCH(CH.sub.2 CH.sub.3).sub.2 ; 1.50(t, 3H, OCH.sub.2CH.sub.3);1.10(m, 6H, SCH (CH.sub.2 CH.sub.3).sub.2Example 15: 8.95(s, 1H, OCH); 5.90(m, 1H, SCH.sub.2 CH.dbd.CH.sub.2);5.36(m, 2H, SCH.sub.2 CH.dbd.CH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.60(m,2H,SCH.sub.2 CH.dbd.CH.sub.2); 3.00(d, 3H NCH.sub.3); 1.40(t, 3H, OCH.sub.2CH.sub.3)Example 16: 9.33(d, 1H, CHS); 4.24(m, 4H, OCH.sub.2 and NCH.sub.2);3.40(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.42(m, 9H, OCH.sub.2CH.sub.3,SCHCH.sub.3 and NCH.sub.2 CH.sub.3); 1.18(m, 3H, SCHOCH.sub.3)CH.sub.2CH.sub.3Example 17: 9.35(d, 1H, CHS); 5.30(dd, 2H, NCH.sub.2 SCH.sub.3); 4.38(m,2H, OCH.sub.2); 3.40(m, 1H, SCH); 2.20(s, 3H, SCH.sub.3); 1.75(m, 2H,SCHCH.sub.2); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.10(m,3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 18: 9.35 (d, 1H, CHS); 4.30(m, 4H, OCH.sub.2 and NCH.sub.2);2.40(d, 3H, SCH.sub.3); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and NCH.sub.2CH.sub.3)Example 19: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);1.50(t, 3H,OCH.sub.2 CH.sub.3) 1.04 (m, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)Example 20: 9.30(d, 1H, CHS); 4.38(m, 2H, OCH.sub.2); 3.60(m, 1H,SCH), 3.35(d, 3H, NCH.sub.3); 1.42(t, 9H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3).sub.2Example 21: 9.35(bd, 1H, CHS); 4.22(m, 2H, OCH.sub.2); 3.38(m, 1H,SCH); 1.70(m, 2H, SCHCH.sub.2); 1.38(m, 6H, OCH.sub.2 CH.sub.3 andSCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3Example 22: 9.30(d, 1H, CHS); 4.20(m, 2H, OCH.sub.2); 3.40(d, 3H,OCH.sub.3); 3.38(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.45(m, 6H,OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 23: 9.35(d, 1H, CHS); 6.00(m, 1H, NCH.sub.2 CH.dbd.CH.sub.2);5.40(m, 2H, NCH.sub.2 CH.dbd.CH.sub.2); 4.38(m, 4H, DNCH.sub.2 andOCH.sub.2);3.38(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.50(m, 6H,OCH.sub.2 CH.sub. 3 and SCHCH.sub.3); 1.05(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 24: 9.30(d, 1H, CHS); 4.36(m, 2H, OCH.sub.2); 3.42(d, 3H,NCH.sub.3); 1.58(d, 9H, SC(CH.sub.3).sub.3 ; 1.42(t, 3H, OCH.sub.2CH.sub.3)
TABLE III (cont.)______________________________________Nuclear Magnetic Resonance Data (ppm, .delta.)______________________________________Example 25: 9.35(d, 1H, CHS); 4.36(m, 2H, OCH.sub.2); 3.38(d, 3H,NCH.sub.3); 3.28(m, 1H, SCH); 1.78(m, 4H, SCH(CH.sub.2 CH.sub.3).sub.2 ;1.40(t, 3H,OCH.sub.2 CH.sub.3); 1.00(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2Example 26: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.40(d, 3H,NCH.sub.3); 3.38(m, 1H, SCH); 1.78(m, 2H, SCHCH.sub.2); 1.50(t, 6H,OCH.sub.2 CH.sub.3) and SCHCH.sub.3); 1.05(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 27: 9.35(d, 1H, CHS); 4.35(m, 2H, OCH.sub.2); 3.90(m, 2H,NCH.sub.2); 3.38(m, 1H, SCH); 1.78(m, 4H, SCHCH.sub.2 andNCH.sub.2 CH.sub.2); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and SCHCH.sub.3);1.00(m, 6H,NCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 28: Not AvailableExample 29: 9.30(d, 1H, CHS); 7.10(m, 5H, aromatic); 5.00(m, 2H,NCH.sub.2); 4.00(m, 2H, OCH.sub.2); 3.38(m, 1H, SCH);1.78(m, 2H, SCHCH.sub.2): 1.50(t, 6H, OCH.sub.2 CH.sub.3 andSCHCH.sub.3);1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 30: 9.30(d, 1H, CHS); 5.10(d, 2H, NCH.sub.2); 4.38(m, 2H,OCH.sub.2); 3.40(m, 1H, SCH); 2.50(S, 3H, NCH.sub.2 SCH.sub.3); 1.75(m,2H,SCHCH.sub.2); 100 (m, SCH(CH.sub.3)--H.sub.2 CH.sub.3)Example 31: 9.35(d, 1H, CHS); 4.30(m, 2H, OCH.sub.2); 3.36(d, 3H,NCH.sub.3); 2.90(m, 2H, SCH.sub.2); 1.38(dt, 6H, OCH.sub.2 CH.sub.3 andSCH.sub.2 CH.sub.3)Example 32: 9.35(d, 1H, CHS); 4.35(m, 2H, OCH.sub.2); 3.35(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);1.50(t, 3H,OCH.sub.2 CH.sub.3); 1.02(t, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)Example 33: 9.30(d, 1H, CHS); 4.38(m, 2H, OCH.sub.2); 3.50(m, 1H,CSCH); 3.36(d, 3H, NCH.sub.3); 1.50(t, 9H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3).sub.2)Example 34: 9.38(d, 1H, CHS); 6.10(m, 1H, NCH.sub.2 CH.dbd.CH.sub.2);5.48(m, 2H, NCH.sub.2 CH.dbd.CH.sub.2); 4.78(m, 2H, SCH.sub.2); 4.40(m,2H,OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.40(m, 6H,OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 35: 9.40(d, 1H, CHS); 4.35(m, 2H, OCH.sub.2); 3.38(m, 1H,SCH); 3.30(d, 3H, NCH.sub.3); 1.75(m, 4H, SCH(CH.sub.2 CH.sub.3); 1.50(t,3H,OCH.sub.2 CH.sub.3); 1.10(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2Example 36: 9.30(d, 1H, CHS); 4.30(m, 4H, OCH.sub.2 and NCH.sub.2);3.40(m, 1H, SCH); 1.80(m, 4H, SCH(CH.sub.2 CH.sub.3).sub.2 ; 1.50(t, 3H,OCH.sub.2 CH.sub.3); 1.08(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2Example 37: 8.90(S, 1H, OCH); 6.00(m, 1H, NCH.sub.2 CH.dbd.CH.sub.2);5.40(m, 2H, NCH.sub.2 CH.dbd.CH.sub.2); 4.38(m, 4H, OCH.sub.2,NCH.sub.2); 3.42(m,1H, SCH) 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCHCH.sub.3); 1.02(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 38: 8.85(S, 1H, CCH); 4.40(dd, 2H, NCH.sub.2 CHCH);4.38(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 2.38(t, 1H, NCH.sub.2 CHCH);1.80(m, 2H, SCHCH.sub.2) 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCHCH.sub.3);1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 39: 8.9(S, 1H, CCH); 4.80(d, 2H, NCH.sub.2); 3.30(m, 2H,OCH.sub.2); 3.38(m, 1H, SCH) 2.30(S, 3H, NCH.sub.2 SCH.sub.3); 1.78(m,2H,SCHCH.sub.2); 1.50 (m, 6H, OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.02(m,3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 44: 8.90(s, 1H, COH); 3.50(m, 3H, OCH.sub.2, SCH); 3.00 (m,2H, NCH.sub.2); 1.78(m, 2H, SCHC .sub.--H.sub.2); 1,50(m, 10H, OCH.sub.2CH.sub.3,SCHCH.sub.3 and NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3); 1.00(m, 6H,SCH(CH.sub.3)CH.sub.2 CH.sub.3and NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).Example 45: 8.70(d, 1H, COH); 8.65 (s, NHCHO); 4.20(m, 2H,OCH.sub.2); 3.38(m, 1H, SCH); 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 6H,OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.02(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3).Example 46: 8.70(s, 1H, COH); 4.68(d, 2H, NCH.sub.2 CN); 4.48(m, 2H,OCH.sub.2); 3.42(m, 1H, SCH); 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 6H,OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.02(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3).Example 49: 8.68(S, 1H, COH); 4.30(m, 2H, OCH.sub.2); 3.10(d, 3H,NCH.sub.3); 2.80(m, 2H, SCH.sub.2); 1.98(m, 1H, SCH.sub.2 CH); 1.48(t,3H,OCH.sub.2 CH.sub.3); 1.00 (d, 6H, SCH.sub.2 CH(CH.sub.3).sub.2).Example 50: 8.70(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.10(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.55(m, 7H, OCH.sub.2 CH.sub.3 andSCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3); 1.00(m, 3H, SCH.sub.2 CH.sub.2CH.sub.2 CH.sub.3).Example 51: 8.70(s, 1H, COH); 4.38(m, 2H, OCH.sub.2); 3.10(d, 3H,NCH.sub.3); 3.05(m, 2H, SCH.sub.2); 1.70(m, 6H, OCH.sub.2 CH.sub.3 andSCH.sub.2 CH.sub.2 CH); 1.10(d, 6H, SCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2.Example 52: 8.80(s, 1H, COH); 4.38(m, 2H, OCH.sub.2); 3.10(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub. 2); 1.70(m, 6H, OCH.sub.2 CH.sub.3 andSCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3); 1.00(m, 6H,SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3).Example 53: 8.75(s, 1H, COH); 4.38(m, 2H, OCH.sub.2); 3.30(m, 1H,SCH); 3.10 (d, 3H, NCH.sub.3); 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 8H,OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.2); 1.00(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3).Example 54: 8.70(s, 1H, COH); 590(m, 1H, SCH.sub.2 CH.sub.2 CH.dbd.CH.sub.2);5.20(m, 2H, SCH.sub.2 CH.sub.2 CH.dbd.CH.sub.2); 4.38(m, 2H, OCH.sub.2);3.20(d,3H, NCH.sub.3); 3.10(m, 2H, SCH.sub.2 CH.sub.3); 2.60(m, 2H, SCH.sub.2);1.50(t, 3H, OCH.sub.2 CH.sub.3).
TABLE III (cont.)______________________________________Nuclear Magnetic Resonance Data (ppm, .delta.)______________________________________Example 55: 8.75(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.70(m, 2H,SCH.sub.2 CH.sub.2 OCH.sub.3); 3.40(s, 3H, SCH.sub.2 CH.sub.2 OCH.sub.3),3.20(d, 3H,NCH.sub.3); 3.15(m, 2H, SCH.sub.2); 1.50(t, 3H, OCH.sub.2 CH.sub.3).Example 56: 8.75(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.60(m, 1H,SCH); 3.00 (d, 3H, NCH.sub.3); 1.78(m, 2H, SCHCH.sub.2); 1.50(m,3H, SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3).Example 57: 8.80(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.70(m, 3H,NCH.sub.2 and SCH); 1.60(m, 7H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.2CH.sub.3).sub.2 ;1.00(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2.Example 58: 8.75(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.60(m, 2H,NCH.sub.2); 2.98(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);1.40(m, 6H,NCH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.3); 1.00(m, 3H, SCH.sub.2CH.sub.2 CH.sub.3)Example 59: 8.75(d, 1H, COH); 8.70(s, 1H, NHCHO); 4.40(m, 2H,OCH.sub.2); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);1.50(m, 3H,OCH.sub.2 CH.sub.3); 1.10 (m, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)Example 60: 8.70(s, 1H, COH); 4.20(m, 2H, OCH.sub.2); 3.65(m, 2H,NCH.sub.2); 4.40(m, 1H, SCH); 1.78(m, 4H, OCH.sub.2 CH.sub.2 andSCH(CH.sub.3)CH.sub.2); 1.40(m, 6H, NCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.00(m,6H, OCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 61: 8.70(s, 1H, COH); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H,SCH); 3.20(d, 3H, NCH.sub.3); 1.80(m, 4H, OCH.sub.2 CH.sub.2 andSCH(CH.sub.3)CH.sub.2); 1.50(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3);1.00(m, 6H,OCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 62: 8.80(s, 1H, COH); 4.80(m, 2H, OCH.sub.2); 3.95(m, 2H,NCH.sub.2); 3.58(m, 1H, SCH); 1.90(m, 2H, SCH(CH.sub.3)CH.sub.2);1.62(m, 6H, NCH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3 );1.20(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 63: 8.70(s, 1H, COH); 5.10(m, 2H, OCH.sub.2 CH.sub.2 F);4.80(m, 2H,OCH.sub.2 CH.sub.2 F); 3.60(m, 1H, SCH); 3.10(d, 3H,NCH.sub.3);1.78(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 3H, SCH(CH.sub.3)); 1.10(m,3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 64: 8.80(s, 1H, COH); 4.38(m, 2H, OCH.sub.2 CH.sub.2 OCH.sub.3);3.90(m, 2H, OCH.sub.2 CH.sub.2 OCH.sub.3); 3.60(s, 3H, OCH.sub.2 CH.sub.2OCH.sub.3);3.30(d, 3H, NCH.sub.3); 1.78(m, 2H, SCH(CH.sub.3)CH.sub.2 CH.sub.3);1.50(m,3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 65: 8.75(s, 1H, COH); 7.00, 6.10 and 5.20(m, 1H,OCH.sub.2 CF.sub.2 CF.sub.2 H); 4.60(m, 2H, OCH.sub.2); 3.60(m, 1H, SCH);3.20(d,3H, NCH.sub.3); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.50(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 66: 9.30(d, 1H, CHS); 7.60(s, 4H, OC.sub.6 H.sub.4 -- 3CF.sub.3);3.50(d,3H, NCH.sub.3) 3.40(m, 1H, SCH); 1.78(m, 2H, SCH(CH.sub.3)CH.sub.2CH.sub.3);1.50(m, 3H, SCH(CH.sub.3)) 1.00 (m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 67: 9.35(d, 1H, CHS); 5.30(dd, 2H, NCH.sub.2 SCH.sub.3); 4.40(m,2H, OCH.sub.2); 3.50(m, 1H, SCH); 2.40(s, 3H, NCH.sub.2 SCH.sub.3);1.78(m,2H, SCH(CH.sub.3)CH.sub.2); 1.60 (m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 68: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,NCH.sub.3); 2.90 (dd, 2H, SCH.sub.2); 2.00(m, 1H, SCH.sub.2 CH); 1.50(t,3H,OCH.sub.2 CH.sub.3); 1.00(d, 6H, SCH.sub.2 CH(CH.sub.3).sub.2)Example 69: 9.35(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);1.58(m, 5H,SCH.sub.2 CH.sub.2 CH.sub.2 and OCH.sub.2 CH.sub.3); 1.00(m, 3H,SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)Example 70: 9.35(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 2.00(m, 1H, SCH.sub.2 CH.sub.2 CH);1.60(m,2H, SCH.sub.2 CH.sub.2); 1.45(t, 3H, OCH.sub.2 CH.sub.3); 1.00(d, 6H,SCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2)Example 71: 9.30(d, 1H, CHS); 4.50(m, 2H, OCH.sub.2); 4.60(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.70(m, 9H, OCH.sub.2 CH.sub.3 andSCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3);1.00 (m, 3H, SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)Example 72: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,NCH.sub.3); 2.90(m, 2H, SCH.sub.2); 2.00(m, 1H, SCH.sub.2 CH(CH.sub.3));1.50(m,8H, OCH.sub.2 CH.sub.3 and SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3);1.00(m,3H, SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3)Example 73: 9.35(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.55(m, 1H,SCH); 3.50 (d, 3H, NCH.sub.3); 2.10(m, 2H, SCH(CH.sub.3)CH.sub.2);1.60(m, 8H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3 )CH.sub.2 CH.sub.2CH.sub.3);1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3)Example 74: 9.30(d, 1H, CHS); 6.00(m, 1H, SCH.sub.2 CH.sub.2 CH.dbd.CH.sub.2);5.30(m, 2H, SCH.sub.2 CH.sub.2 CH.dbd.CH.sub.2); 4.50(m, 2H, OCH.sub.2);3.50(d,3H, NCH.sub.3); 3.10(m, 2H, SCH.sub.2 CH.sub.2 CH.dbd.CH.sub.2); 2.65(m,2H,SCH.sub.2); 1.60(t, 3H, OCH.sub.2 CH.sub.3).Example 75: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.60(m, 2H,SCH.sub.2 CH.sub.2 OCH.sub.3); 3.45(s, 3H, SCH.sub.2 CH.sub.2 OCH.sub.3);3.40(d, 3H,NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.45(t, 3H, OCH.sub.2 CH.sub.3)Example 76: 9.30(d, 1H, CHS); 4.60(m, 2H, OCH.sub.2); 3.60(d,3H, NCH.sub.3); 3.62(m, 1H, SCH); 1.78(m, 2H, SCH(CH.sub.3)CH.sub.2);1.50(m, 3H, SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 77: 9.30(d, 1H, CHS); 4.40(m, 4H, OCH.sub.2, NCH.sub.2);3.50(m, 1H, SCH); 1.80(m, 4H, OCH.sub.2 CH.sub.2 and SCH(CH.sub.3)CH.sub.2);1.50(m, 6H, NCH.sub. 2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3);1.10(m, 6H, OCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 78: 9.30(d, 1H, CHS); 4.30(m, 2H, OCH.sub.2); 3.50(d, 3H,NCH.sub.3); 3.50(m, 1H, SCH); 1.80(m, 4H, SCH(CH.sub.3)CH.sub.2 andOCH.sub.2 CH.sub.2); 1.50(t, 3H, SCH(CH.sub.3)); 1.00(m, 6H,SCH(CH.sub.3)CH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.2 CH.sub.3)
TABLE III (cont.)______________________________________Nuclear Magnetic Resonance Data (ppm, .delta.)______________________________________Example 79: 9.30(d, 1H, CHS); 4.90(d, 2H, NCH.sub.2); 4.40(m, 2H,OCH.sub.2); 3.80(s, 3H, NCH.sub.2 CO.sub.2 CH.sub.3); 3.50(m, 1H, SCH);1.80(m,2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 80: 9.28(d, 1H, CHS); 7.40(m, 5H, NCH.sub.2 C.sub.6 H.sub.5);5.65(m, 2H,NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)CH.sub.2);1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 81: 9.30(d, 1H, CHS); 7.40(m, 4H, NCH.sub.2 C.sub.6 H.sub.4 F);5.50(m,2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m,2H, SCH(CH.sub.3)CH.sub.2); 1.50 (m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)CH.sub.2); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 82: 9.30(d, 1H, CHS); 7.20(m, 4H, NCH.sub. 2 C.sub.6 H.sub.4OCH.sub.3); 5.40(m, 2H, NCH.sub.2); 4.30 (m, 2H, OCH.sub.2); 3.98(s, 3H, NCH.sub.2C.sub.6 H.sub.4 OCH.sub.3);3.30(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H,OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2); 1.00 (m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 83: 9.30(d, 1H, CHS); 7.60(m, 4H, NCH.sub.2 C.sub.6 H.sub.4CF.sub.3);5.70(m, 2H, NCH); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m,2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)CH.sub.2); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 84: 9.25(d, 1H, CHS); 4.50(d, 2H, NCH.sub.2); 4.40(m, 2H,OCH.sub.2); 3.70(t, 2H, NCH.sub.2 CH.sub.2 CH.sub.2 Cl); 3.38(m, 1H,SCH); 2.40(m, 2H,NCH.sub.2 CH.sub.2); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H,OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 85: 9.30(d, 1H, CHS); 7.50(m, 4H, NCH.sub.2 SC.sub.6 H.sub.4Cl);4.40(m, 2H, OCH.sub.2); 3.60(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 86: 9.30(d, 1H, CHS); 5.60(m, 2H, NCH.sub.2 C(Br).dbd.CH.sub.2);5.00(NCH.sub.2); 4.50(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50 (m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)CH.sub.2);1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 87: 9.30(d, 1H, CHS); 7.40(m, 5H, NCH.sub.2 CH.dbd.CHC.sub.6H.sub.5);6.60(m, 2H, CH.sub.2 CH.dbd.CH); 5.00(m, 2H, NCH.sub.2); 4.30(m, 2H,OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);1.50(m, 6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.00(m,3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 88: 9.30(d, 1H, CHS); 5.00(d, 2H, NCH.sub.2); 4.60(m, 4H,OCH.sub.2 and NCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3); 3.60(m, 1H, SCH);1.80(m,2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 9H, OCH.sub.2 CH.sub.3, NCH.sub. 2CO.sub.2 CH.sub.2 CH.sub.3and SCH(CH.sub.3); 1.20(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 89: 9.30(d, 1H, CHS); 4.38(m, 2H, OCH.sub.2 CH.sub.2); 3.60(m,2H, OCH.sub.2 CH.sub.2 OCH.sub.3); 3.39(d, 3H, NCH.sub.3); 3.38(s, 3H,OCH.sub.3);3.38(m, 1H, SCH); 1.80 (m, 2H, SCH(CH.sub.3)CH.sub.2); 1.38(t, 3H,SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 90: 9.35(d, 1H, CHS); 7.00, 6.00 and 5.20(m, 1H,HCF.sub.2 CH.sub.2); 4.58 (m, 2H, OCH.sub.2 CF.sub.2 CF.sub.2 H); 3.50(m,1H, SCH);3.50(d, 3H, NCH.sub.3); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(t, 3H,SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 91: 9.35(d, 1H, CHS); 4.60(m, 2H, OCH.sub.2 CF.sub.3); 3.60(m,1H,SCH); 3.60(m, 2H, NCH.sub.2); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);1.60(m,3H, SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 92: 9.30(d, 1H, CHS); 7.40(m, 5H, NCH.sub.2 SC.sub.6 H.sub.5);5.60(d,2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.60(m, 1H, SCH); 1.80(m,2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 3H, OCH.sub.2 CH.sub.3,SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 93: 9.30(d, 1H, CHS); 5.98(m, 2H, NCH.sub.2 CH.dbd.CHCH.sub.3);4.90 (m, 2H OCH.sub.2); 4.60(m, 2H, NCH.sub.2); 3.50(m, 1H, SCH);1.90(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.80(m, 3H, NCH.sub.2 CH.dbd.CHCH.sub.3);1.60(m, 3H, OCH.sub.2 CH.sub.3, SCH(CH.sub.3)); 1.10(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 94: (d, 1H, CHS); 7.80(m, 4H, NCH.sub.2 C.sub.6 H.sub.4); 5.40(m,2H,NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.30(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 121: 8.90(s, 1H, CHO); 4.40(d, 2H, NCH.sub.2); 4.38(m, 2H,OCH.sub.2); 3.85(s, 3H, NCH.sub.2 CO.sub.2 CH.sub.3); 3.50(m, 1H, SCH);1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.60(m, 9H, OCH.sub.3, OCH.sub.2 CH.sub.3,SCH(CH.sub.3 ); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 122: 8.85(s, 1H, CHO); 7.50(m, 5H, NCH.sub.2 CH.sub.6 H.sub.5);5.00(dd, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 6H, OCH.sub.3 andSCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 123: 8.85(s, 1H, CHO); 7.40(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);4.90(m,2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.60(m, 6H, OCH.sub.3 and SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 124: 8.90(s, 1H, CHO); 7.30(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);5.00(dd, 2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.90(s, 3H, OCH.sub.3);3.59(m, 1H, SCH); 1.80 (m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m,6H, OCH.sub.3 and SCH(CH.sub.3)); 1.00(m, 3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 125: 8.85(s, 1H, CHO); 7.80(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);5.00(dd,2H, NCH.sub.2); 4.38(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.59(m, 6H, OCH.sub.3 and SCH(CH.sub.3)); 1.10(m,3H,SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 126: 8.90(s, 1H, CHO); 4.40(m, 2H, OCH.sub.2); 3.90(m, 2H,NCH.sub.2); 3.80(m, 2H, NCH.sub.2 CH.sub.2 CH.sub.2 Cl); 3.409m, 1H,SCH);2.38(m, 2H, NCH.sub.2 CH.sub.2); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);1.55(m, 6H,OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10 (m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 127: 8.90(s, 1H, CHO); 7.40(m, 4H, NCH.sub.2 SC.sub.6 H.sub.4);5.00(d,2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.75(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.40(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 128: 8.90(s, 1H, CHO); 5.90(m, 2H, NCH.sub.2 C(BR).dbd.CH.sub.2);4.60(m, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3) CH.sub.2); 1.55(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)
TABLE III (cont.)______________________________________Nuclear Magnetic Resonance Data (ppm, .delta.)______________________________________Example 129: 8.90(s, 1H, CHO); 7.40(s, 5H, NCH.sub.2 CH.dbd.CHC.sub.6H.sub.5);6.80(d, 1H, NCH.sub.2 CH.dbd.CH); 6.40(m, 1H, NCH.sub.2 CH.dbd.CH);4.60(m, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m, 6H, OCH.sub.2 CH.sub.3and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 130: 8.90(s, 1H, CHO); 4.40(d, 2H, NCH.sub.2); 4.38(m, 4H,OCH.sub.2 and NCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3); 3.50(m, 1H, SCH);1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.55 (m, 9H, OCH.sub.2 CH.sub.3, NCH.sub.2CO.sub.2 CH.sub.2 CH.sub.3and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3) CH.sub.2 CH.sub.3)Example 131: 8.85(s, 1H, CHO); 8.00(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);5.00(d,2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.45(m, 1H, SCH); 1.80(m,2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 132: 8.90(s, 1H, CHO); 7.80(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);5.00(dd,2H, NCH.sub.2); 3.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3) CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 133: 8.90(s, 1H, CHO); 8.00(m, 5H, NCH.sub.2 COC.sub.6 H.sub.5);5.20(d, 2H, NCH.sub.2); 3.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m, 6H, OCHCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 134: 8.90(s, 1H, CHO); 7.50(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);5.00(d, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH),1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 135: 8.90(s, 1H, CHO); 7.30(m, 4H, NCH.sub.2 OC.sub.6 H.sub.4);5.70(d, 2H, NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 136: 8.90(s, 1H, CHO); 7.78(m, 7H, NCH.sub.2 C.sub.10 H.sub.7);5.10(dd, 2H, NCH.sub.2); 4.00(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 137: 8.90(s, 1H, CHO); 5.80(m, 2H, NCH.sub.2 CH.dbd.CHCH.sub.3);4.40(m, 4H, OCH.sub.2 and NCH.sub.2); 3.40(m, 1H, SCH);1.90(m, 5H, SCH(CH.sub.3) and NCH.sub.2 CH.dbd.CHCH.sub.3 ; 1.50(m,6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 138: 8.90(s, 1H, CHO); 7.48(m, 3H, NCH.sub.2 C.sub.6 H.sub.3);5.30(dd,2H, NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 139: 8.85(s, 1H, CHO); 5.10(d, 2H, NCH.sub.2); 4.40(m, 2H,OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);1.50(m,6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 140: 8.90(s, 1H, CHO); 4.40(m, 2H, OCH.sub.2); 3.50(m, 2H,NCH.sub.2); 2.75(m, 2H, SCH.sub.2); 1.50(m, 9H, NCH.sub.2 CH.sub.2CH.sub.2 CH.sub.3,OCH.sub.2 CH.sub.3 and SCH.sub.2 CH.sub.2 CH.sub.3);1.00(m, 6H, SCH.sub.2 CH.sub.2 CH.sub.3 and NCH.sub.2 CH.sub.2 CH.sub.2CH.sub.3)Example 141: 8.90(s, 1H, CHO); 7.39(m, 5H, NCH.sub.2 C.sub.6 H.sub.5);4.80(m,2H, NCH.sub.2); 4.00(m, 2H, OCH.sub.2); 2.70(m, 2H, SCH.sub.2); 1.70(m,2H,SCH.sub.2 CH.sub.2); 1.20(m, 6H, SCH.sub.2 CH.sub.2 CH.sub.3 andOCH.sub.2 CH.sub.3)Example 142: 8.90(s, 1H, CHO); 4.40(m, 6H, NCH.sub.2, OCH.sub.2,NCH.sub.2 CO.sub.2 CH.sub.2); 3.00(m, 2H, SCH.sub.2); 1.70(m, 2H,SCH.sub.2 CH.sub.2); 1.20(m, 9H, SCH.sub.2 CH.sub.2 CH.sub.3, OCH.sub.2CH.sub.3and NCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3)Example 143: 8.85(s, 1H, CHO); 4.60(m, 4H, OCH.sub.2 and NCH.sub.2);3.90(m, 2H, NCH.sub.2 CH.sub.2 CH.sub.2 Cl); 3.10(m, 2H, SCH.sub.2);2.20(m, 2H,NCH.sub.2 CH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2); 1.50(m, 3H,OCH.sub.2 CH.sub.3); 1.00(m, 3H, SCH.sub.2 CH.sub.2 CH.sub.2)Example 144: 8.90(s, 1H, CHO); 7.80(m, 9H,NCH.sub.2 C.sub.6 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5); 5.30(s, 2H,NCH.sub.2 C.sub.6 H.sub.4 OCH.sub.2);5.00(m, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH);1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 146: 8.90(s, 1H, CHO); 5.10(m, 2H, NCH.sub.2 C(CH.sub.3).dbd.CH.sub.2);4.30 (m, 4H, OCH.sub.2 and NCH.sub.2); 3.50(m, 1H, SCH); 1.80(s, 3H,NCH.sub.2 C(CH.sub.3).dbd.CH.sub.2); 1.45(m, 6H, OCH.sub.2 CH.sub. 3 andSCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 148: 8.90(s, 1H, CHO); 7.50(s, 5H, NCH.sub.2 C.sub.6 H.sub.5);5.00(dd,2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3) CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 152: 8.90(s, 1H, CHO); 7.38(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);4.78(m,2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 159: 8.85(s, 1H, CHO); 8.00(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);4.90(dd,2H, NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)Example 165: 8.90(s, 1H, CHO); 5.00(m, 2H, NCH.sub.2); 4.38(m, 2H,OCH.sub.2 ); 3.50(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);1.50(m,6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3Example 176: 8.90(s, 1H, CHO); 8.00(m, 3H, NCH.sub.2 C.sub.6 H.sub.3);4.90(dd,2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 2.70(s, 3H,NCH.sub.2 C.sub.6 H.sub.3 CH.sub.3); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);1.50(m, 6H,OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10 (m, 3H, SCH(CH.sub.3)CH.sub.2CH.sub.3)Example 180: 8.85(s, 1H, CHO); 7.70(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);4.90(dd,2H, NCH.sub.2); 4.39(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 andSCH(CH.sub.3));1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)______________________________________
Table IV which follows sets forth the biological data obtained as described above for the exemplary compounds described in Table I.
______________________________________Code Symbol Common Name Latin Name______________________________________TSM Two-spotted spider mite Tetranychus urticaeGPA Green peach aphid Myzus persicaeCRW Southern corn rootworm Diabrotica un- decimpunctata howardiNEMA Southern root-knot nematode Meloidogyne incognita______________________________________
A test solution containing 600 ppm of test compound in a solvent (acetone:methanol, 1:1) and then adding water to give an acetone:methanol:water system of 5:5:90. A test solution containing 150 ppm of test compound is prepared by diluting 1 part of 600 ppm test solution with three parts of water. A 1:1 mixture of alkylarlpolyetheralcohol (commercially available under the trademark TRITON.RTM. X-155) and a modified phthalic glycerol alkyl resin (commercially available under the trademark TRITON.RTM. B-1956) is utilized at the equivalent of one ounce per 100 gallons of test solution as a surfactant.
For the mite test, infested bean (Phaseolus limeanus) leaf section (.about.1.times.1 inches) containing about 50 mites are placed in a Petri dish lid on a moistened piece of cotton. The leaves are then sprayed with the 600 ppm test solution using a rotating turntable. They are held for 24 hours and then the percent kill is determined.
For the aphid test, infected broccoli (Brassica oleracea) leaf section (.about.1.times.1 inches) containing about 30 adult and mymphal aphids are placed in a Petri dish lid on a moistened piece of cotton. The leaves are then sprayed with the 600 ppm test solution using a rotating turntable. They are held for 24 hours and then the percent kill is determined.
For the rootworm larvae test, ten milliliters of the 150 ppm test solution are added to 200 milliliter of soil in a 16 oz. jar to give a concentration by volume of about 8 ppm. The jar is shaken to insure thorough mixing, immediately uncapped, and allowed to ai for 2 hours. Two presoaked kernels of Golden Cross Bantam corn (Zea map) are placed in the bottom of a 1 oz. plastic cap and covered with about 30 grams of treated soil. The soil surface is inoculated with approximately 120 southern corn rootworm eggs and the plastic cup closed iwth a tight-fitting cap. The test cup is held for 10 days at 27.degree. C. and then the percent kill relative to the untreated check is determined.
For the nematode test, soil is homogenously inoculated with nematode eggs at the rate of about 5000 eggs per 200 milliliters of soil extracted from a macerated blend of tomato roots heavily knotted with the root knot nematode. Ten milliliters of the 150 ppm test solution are added to 200 milliliters of the inoculated soil in a 16 oz. jar to give a concentration by volume of about 8 ppm. The jar is shaken to insure thorough mixing, immediatley uncapped, and allowed to air for 24 hours. The soil is then placed into a 3-inch plastic pot after which time 3 cucumber (Cucumis sativus) seeds are planted. About 23 days thereafter, the cucumber plants are removed from the soil and root system examined for the presence of knots. A total of 25 knots or less is considered as a measure of control. Excellent control is characterized by 0-2 knots.
TABLE IV______________________________________Pesticidal Activity % Control.sup.a Soil Application Foliar Application (150 ppm) (600 ppm)Example CRW NEMA TSM GPA______________________________________ 1 100 +++++ 100 98 2 100 -- 100 50 3 100 -- 0 0 4 62 -- 0 0 5 65 +++++ 100 100 6 100 +++++ 100 100 7 100 +++++ 100 100 8 27 +++++ 0 0 9 100 +++ 100 95 10 100 -- 100 NA 11 100 -- 100 100 12 98 +++++ 81 0 13 100 -- 100 100 14 100 ++++ 100 100 15 0 -- 84 0 16 100 -- 100 100 17 18 100 ++++ 100 73 19 20 21 22 -- 0 0 22 100 +++++ 100 100 23 100 +++++ 100 0 24 100 +++++ 100 0 25 100 +++++ 100 100 26 100 +++ 100 100 27 100 +++++ 100 100 28 100 +++++ 100 100 29 100 +++++ 100 100 30 100 +++++ 100 100 31 100 ++++ 100 100 32 100 +++++ 100 100 33 100 +++++ 100 100 34 100 +++ 100 100 35 100 +++++ 100 100 36 100 NA 100 100 37 100 +++++ 100 100 38 100 +++++ 100 100 39 100 +++++ 100 100 40 100 -- 100 95 41 100 +++++ 100 100 42 100 +++++ 100 100 43 44 100 +++++ 100 100 45 100 -- 89 100 46 100 +++++ 100 100 47 100 +++++ 100 100 48 100 +++++ 100 100 49 100 +++ 100 100 50 100 -- 100 76 51 97 NA NA NA 52 100 +++ 100 0 53 100 ++++ 100 0 54 96 -- 100 29 55 100 -- 100 NA 56 100 +++++ 100 NA 57 100 -- 100 100 58 100 +++ 100 100 59 100 -- 100 40 60 100 -- 0 100 61 100 ++ 59 100 62 100 -- 97 0 63 100 NA 100 100 64 94 -- 100 100 65 100 +++++ 100 83 66 100 -- 100 100 67 100 ++++ 100 73 68 100 +++ 100 100 69 100 -- 100 11 70 100 -- 100 0 71 83 -- 100 93 72 100 -- 100 100 73 100 -- 100 100 74 70 -- 100 100 75 100 -- 100 100 76 100 ++++ 100 100 77 100 -- 0 100 78 100 -- 51 100 79 99 NA 100 100 80 100 ++ 100 100 81 100 -- 100 100 82 100 -- 100 100 83 100 ++ 100 100 84 100 -- 100 100 85 100 -- 100 100 86 100 -- 100 100 87 100 +++ 100 100 88 100 +++ 100 100 89 82 +++++ 100 100 90 100 +++++ 100 100 91 100 +++++ 33 0 92 100 -- 100 100 93 100 -- 100 100 94 99 -- 100 100 95 100 +++++ 100 100 96 100 -- 100 100 97 100 -- 100 100 98 100 +++++ 100 100 99 89 +++++ 100 91100 100 ++++ 100 100101 100 -- 100 100102 100 +++++ 100 100103 100 -- 100 100104 100 ++++ 100 100105 100 ++++ 100 100106 100 +++ 100 100107 100 +++++ 100 100108 100 +++++ 100 100109 100 +++++ 100 100110 97 -- 100 100111 99 ++++ 100 100112 100 +++ 100 100113 100 +++++ 100 100114 100 +++++ 100 100115 100 +++++ 100 100116 98 +++++ 100 100117 100 +++ 100 100118 100 -- 100 100119 95 +++ 100 100120 90 -- 100 100121 98 +++++ 100 100122 100 ++++ 100 100123 100 ++ 100 100124 100 -- 100 100125 100 -- 100 100126 100 -- 100 100127 100 -- 100 100128 100 +++ 100 NA129 100 -- 100 100130 100 -- 100 100131 100 -- 100 100132 100 -- 100 100133 100 -- 100 100134 100 -- 100 100135 100 -- 100 100136 100 -- 100 100137 100 -- 100 95138 100 -- 100 100139 100 -- 100 100140 100 ++ 100 100141 100 -- 100 100142 100 ++++ 100 100143 100 ++ 100 100144 98 -- 100 100145 100 -- 100 100146 100 ++ 100 100147 100 100 100148 100 100 100149 100 +++ 100 100150 100 +++++ 100 100151 100 +++++ 100 100152 100 +++++ 100 100153 100 +++++ 100 100154 100 +++++ 100 100155 100 ++++ 100 100156 100 +++++ 100 100157 100 +++++ 100 100158 100 +++++ 100 100159 99 + +++ 100 100160 100 +++++ 100 100161 98 +++++ 100 100162 98 +++++ 100 100163 100 +++++ 100 100164 100 +++++ 100 100165 100 +++++ 100 100166 100 +++ 100 100167 100 +++++ 100 100168 100 +++++ 100 100169 100 +++++ 100 100170 100 100 100171 94 +++++ 100 100172 98 +++++ 100 100173 100 +++++ 100 100174 100 +++++ 100 100175 100 +++++ 100 100176 98 +++++ 100 100177 100 +++++ 100 100178 100 +++ 100 100179 100 +++++ NT NT180 0 +++++ 100 100______________________________________CRW = Southern Corn RootwormNEMA = Southern Root Knot NematodeTSM = Two Spotted Spider MiteGPA = Green Peach AphidNA = Not Available______________________________________ Rank Knots______________________________________ +++++ 0-2 ++++ 3-6 +++ 7-9 ++ 18-25 - 25+______________________________________ .sup.a CRW, TSM, & GPA Test results expressed as % control. NEMA Test results expressed as rankings for degree of knotting.

Number	Name	Date
3399213	Osborne	Aug 1968
3511635	Braxton, Jr. et al.	May 1970
3657426	Schroeder	Apr 1972
3716600	Magee	Feb 1973
3760043	Kishino et al.	Sep 1973
3825634	Magee	Jul 1974
3845172	Magee	Oct 1974
3885032	Magee	May 1975
3914417	Magee	Oct 1975
4049679	Magee	Sep 1977
4110443	Magee	Aug 1978
4161524	Kishino et al.	Jul 1979
4263288	Ollinger	Apr 1981
4544553	Smolanoff et al.	Oct 1985

Pesticidal phosphoroamido(di)thioates

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Parent Case Info

US Referenced Citations (14)

Non-Patent Literature Citations (2)

Divisions (1)

Continuation in Parts (1)

Entry
Soviet Inventors Illustrated (Derwent Publication 1980), Week C05, Section C, p. 1, Abstract No. 08617C/05.
Derwent Abstract of Japans 70 12281 4/6/77.