Application of Payne

Decision Date13 September 1979
Docket NumberPatent Appeal No. 77-522.
Citation606 F.2d 303
CourtU.S. Court of Customs and Patent Appeals (CCPA)
PartiesIn the Matter of the Application of Linwood K. PAYNE, Jr., Deceased by Betty Lou Payne, Executrix, John A. Durden, Jr. and Mathias H. J. Weiden, Appellants.

Robert C. Brown, Aldo J. Cozzi, New York City, attorneys of record, for appellants; James C. Arvantes, Arlington, Va., of counsel.

Joseph F. Nakamura, Washington, D. C., for the Commissioner of Patents; Gerald H. Bjorge, Washington, D. C., of counsel.

Before MARKEY, Chief Judge, RICH, BALDWIN and MILLER, Judges, and RE,* Chief Judge.

MARKEY, Chief Judge.

Payne et al. (Payne) appeal from the decision of the Patent and Trademark Office (PTO) Board of Appeals (board) sustaining the rejection under 35 U.S.C. § 103 of claims 1-12 of application serial No. 254,271, filed May 17, 1972, for "Pesticidal Compositions." We affirm.

The Invention

Payne invented five, six, and seven member heterocyclic carbamoyloximino compounds having pesticidal activity. The claims on appeal are:

1. As new compositions of matter compounds having the structural formula:
wherein:
R1 is hydrogen or alkyl having from 1 to 4 carbon atoms;
R2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen substituted lower alkyl, lower alkoxyalkyl, lower alkylthioalkyl, lower alkoxy, phenyl, lower alkyl substituted phenyl, lower phenyl alkyl or halogen substituted phenyl;
R3 and R4 may be the same or different and are hydrogen, lower alkyl having from 1 to 6 carbon atoms, lower alkenyl having from 2 to 6 carbon atoms, halogen substituted alkyl having from 1 to 6 carbon atoms, alkoxyalkyl having a total of from 2 to 6 carbon atoms, alkylthioalkyl having a total of 2 to 6 carbon atoms, phenyl, lower alkylphenyl, halogen substituted phenyl, or lower alkoxyphenyl;
A is methylene, ethylene, propylene, ethenylene, propenylene or methylene, ethylene, propylene, ethenylene, or propenylene substituted with one or more alkyl groups having from 1 to 3 carbon atoms; and
x is 0, 1 or 2.
2. Compositions as claimed in claim 1 wherein A is methylene.
3. Compositions as claimed in claim 1 wherein A is ethylene.
4. Compositions as claimed in claim 1 wherein A is propylene.
5. Compositions as claimed in claim 1 wherein R1 is hydrogen and R2 is methyl.
6. 5,5-Dimethyl-4-(methylcarbamoyloximino)-1,3-dithiolane.
7. 2-(Carbamoyloximino)-1, 4-dithiane.
8. 2-(Methylcarbamoyloximino)-1, 4-dithiane.
9. 3-Methyl-2-(methylcarbamoyloximino)-1, 4-dithiane.
10. 3,3-Dimethyl-2-(methylcarbamoyloximino)-1, 4-dithiane.
11. 2-(Methylcarbamoyloximino)-4-oxo-1, 4-dithiane.
12. 3,3-Dimethyl-2-(methylcarbamoyloximino)-1, 4-dithiene-5.

The Rejection — Structure and Properties

The principal references relied upon by the examiner were:

                  Addor (Addor I)                  3,193,561    July 6, 1965
                  Addor (Addor II)                 3,365,361    January 23, 1968
                  Addor (Addor III)                3,467,672    September 16, 1969
                  Ghosh et al. (Ghosh)             3,661,930    May 9, 1972
                  Nikles                           3,678,075    July 18, 1972
                

Addor I discloses pesticidal compounds with five or six member heterocyclic rings containing two sulfur atoms and a carbamoyloximino moiety, as exemplified by the general structure:

Addor II discloses a group of pesticides, all with six member heterocyclic rings containing two sulfur atoms and a carbamoy-loximino moiety, having the structure:

Addor III discloses pesticides structurally identical to the Addor I five-membered ring compounds except that the ring is unsaturated.

Ghosh discloses pesticidal compounds with seven member heterocyclic rings containing two sulfur atoms and a carbamoyloximino moiety, as exemplified by the structure:

Nikles discloses pesticides structurally identical to the Addor I five-membered ring compounds except that an alkenyl substituent is attached to the ring.

The claimed compounds differ from the primary reference compounds only in the sulfur-carbamoyloximino moiety linkage. In the claimed compounds, one sulfur is linked directly to the carbamoyloximino moiety and the other sulfur is linked directly to an intervening carbon atom, which is in turn linked directly to the carbamoyloximino moiety. In the primary references, both sulfur atoms are linked directly either to the carbamoyloximino moiety (Addor I; Addor III; Nikles) or to intervening carbon atoms which are in turn linked directly to the carbamoyloximino moiety (Addor II; Ghosh).

The secondary references were:

                  Walsh               3,564,013     February 16, 1971
                  Japanese patent     40-2073       February 3, 1965
                  Haubein             2,766,166     October 9, 1956
                  German patent       1,203,797     October 28, 1965
                

Walsh discloses pesticidal phosphonated heterocyclic mercaptal compounds, exemplified by the structure:

The Japanese patent discloses pesticidal dithiophosphate compounds, exemplified by the structure:

Haubein discloses pesticidal dithiophosphate compounds having the structural formula:

The secondary references were cited for their disclosure that phosphonated dithiacycloalkanes exhibit pesticidal activity when substituted at any ring position. The examiner related the principal references' showing of carbamoyloximino substituted2 dithiacycloalkanes as pesticides with the Walsh, Haubein, and Japanese patent suggestion "that the carbamoyloximino group may equivalently substitute any position on the heterocyclic ring." The German patent was cited for its teaching that the sulfur atom in thiacycloalkane pesticides may be equivalently oxidized.

The examiner rejected claims 1-11 as obvious in view of each of Addor I, Addor II, and Ghosh; claims 1-5 as obvious in view of Nikles; claims 1 and 12 as obvious in view of Addor III; and all claims as obvious in view of Addor I, Addor II, Ghosh, Addor III, and Nikles in view of Walsh, Haubein, the Japanese patent, and the German patent.3 The fundamental basis for each rejection was that the claimed compounds are position isomers or methylene ring homologs of the compounds of the principal references, having a close structural similarity to, and a community of properties with, the principal reference compounds.

Payne presented the affidavit of coinventor Durden,4 Table I of which allegedly illustrates lack of structural obviousness in differences between the oxidation states of the two sulfur atoms in the claimed compounds and the oxidation states of the two sulphur atoms in prior art compounds. Table II purportedly establishes an unexpectedly superior scope and level of pesticidal activity of the claimed compounds in a comparison of "the most representative compound of Addor I" with four of Payne's compounds:

TABLE II

Table III presents insect toxicity data for four compounds said to be closely related to the Addor II compounds by virtue of the sulfur atoms and oximino-substituted carbon atoms having the same oxidation states.6 Durden concluded from Table III that the Addor II compounds, and the Ghosh compounds (homologs of the Addor II compounds), were ineffective pesticides except for limited activity against aphid and housefly. Table V,7 comparing two of Payne's compounds with their "linear or aliphatic analogs" and reflecting erratic activity of linear compounds and their inactivity against armyworm, is said to illustrate unique broad spectrum activity in the claimed compounds:

TABLE V

The examiner found Durden's affidavit insufficient:

The test results reported in Table II of the first Durden Affidavit cannot be seen to establish the unobviousness of the presently claimed compounds over Addor I. The Addor I compounds are superior to the closest structurally related compounds of the present invention, designated as Applicants-1, Applicants-2, Applicants-3 and Applicants-4, in their effect on aphids and houseflies, i. e., the claimed compounds required applications of from 4 to 65 times greater than the Addor I compound to effect the same kill. Although Applicants-1, Applicants-2, Applicants-3 and Applicants-4 do show a greater toxicity against mites, armyworms and bean beetles, it is noted that there is as much or greater difference observed among the compounds of the present application as there is between the compounds of the present application and Addor I. Note the greater differences in toxicity between the homologous compounds Applicants-3 and Applicants-4 as compared to the lesser differences in toxicity between the Applicants-3 and the isomeric compound of Addor I. Such wide variation of toxicities cannot be seen to establish the unobviousness of the presently claimed compounds as a whole over the Addor I compounds.
No information has been presented comparing the claimed compounds with those of Addor II, Ghosh, Addor III or Nikles and the present claims thus remain validly rejected thereover.
The results reported in Tables III through V of the first Durden Affidavit do not compare the claimed compounds with compounds of the references of record in this rejection and garner Appellants nothing in their attempt to demonstrate patentability over the prior art.
The Board

The board agreed with the examiner that the claimed compounds would have been prima facie obvious from either their close structural similarity to prior art pesticides or from the combination therewith of the secondary references teaching that dithiacycloalkane pesticidal compounds may be substituted at any ring position, albeit with a different substituent.

In response to Payne's challenge to the examiner's conclusion of structural obviousness the board stated:

The challenge is based on an allegation that the claimed compounds are not true isomers or homologs of prior art compounds since the oxidation states of the oximino substituted carbon atom and the ring sulfur atoms are different in the prior art compounds. It is urged that, in the absence of such a true isomeric or homologous relationship, the legal conclusion of structural
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