Pesticidal sulfur compounds

Details Pesticidal sulfur compounds Pesticidal sulfur compounds

1998-06-16

2000-10-24

Ramsuer, Robert W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514404, 514407, 546279, 548119, 5483235, 5483245, 5483667, 5483684, 5483691, 5483701, 548541, 548544, A01N 4356, C07D23144

Patent

active

061369837

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new sulfur compounds, including sulfilimines and sulfoximines intermediates thereto, and processes to prepare the compounds. The invention further pertains to compositions of said compounds and methods, using said compounds, for the control of arthropod, nematode, helminth or protozoan pests. In particular, it pertains to the application of compounds or compositions thereof in agricultural methods of use, particularly as pesticides.
In the instant specification, the word sulfilimine is used to name compounds comprising the group ##STR2## In the instant specification, the word sulfoximine is used to name compounds comprising ##STR3##
Various pesticidal pyrazoles, pyrroles, and imidazoles have been disclosed: European Patent Publication No 418016; European Patent Publication No 403309; U.S. Pat. No. 5,104,994; European Patent Publication No 352944; U.S. Pat. No. 5,079,370; U.S. Pat. No. 5,047,550; U.S. Pat. No. 5,232,940; U.S. Pat. No. 4,810,720; U.S. Pat. No. 4,804,675; U.S. Pat. No. 5,306,694; U.S. Pat. No. 4,614,533; WPO Publication No. WO 93/06089; and WPO Publication No. WO 94/21606 describe pesticidal (4-pyrazolyl) sulfides, sulfoxides and sulfones. U.S. Pat. No. 5,187,185 describes 4-pyrrolyl sulfides, sulfoxides and sulfones. U.S. Pat. No. 5,223,525 describes pesticidal 4-imidazolyl sulfides, sulfoxides and sulfones.
Due to the many existing pests and crops and conditions of attacks of crops by pests, there is a need for further novel pesticidal compounds.
In one aspect, the present invention provides compounds for use in controlling arthropod, nematode, helminth and protozoan pests, said compounds having the general formula: ##STR4## wherein: .dbd.X is .dbd.NR.sup.3, .dbd.O or an electron pair (it being understood that, in this situation, another way to represent Formula (I) is to delete .dbd.X); -C.sub.8 (cycloalkyl)alkyl, each of which is optionally substituted by one or more halogen; alkyl; C.sub.1 -C.sub.6 haloalkyl; COR.sup.4 ; S(O).sub.p R.sup.4 ; CN; NO.sub.2 ; COOR.sup.4 ; CONR.sup.4 R.sup.5 ; C(O)SR.sup.4 ; C(S)OR.sup.4 ; SO.sub.2 NR.sup.4 R.sup.5 ; P(O).sub.q (R.sup.4)(R.sup.5); P(O).sub.q (OR.sup.4)(R.sup.5); P(O).sub.q (OR.sup.4)(OR.sup.5); C.dbd.(NR.sup.4)NR.sup.5 R.sup.6 ; CH.dbd.NR.sup.4 ; C.dbd.(NR.sup.4)(OR.sup.5); C(S)N(R.sup.4)(R.sup.5); C(O)C(O)R.sup.4 ; C(O)C(O)OR.sup.4 ; C(O)C(O)NR.sup.4 R.sup.5 ; and CONR.sup.4 SO.sub.2 R.sup.5 ; CN; CHO; R.sup.14 ; phenyl optionally substituted by one or more of R.sup.14, halogen, CN, NO.sub.2, OR.sup.14, SR.sup.14, COR.sup.14, COOR.sup.14, or OR.sup.14 ; halogen; COR.sup.14 ; COOR.sup.14 ; CHO; and OH; ##STR5## R.sup.7 is CN, NO.sub.2, H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, halogen, CHO, or COR.sup.20, R.sup.7 ; R.sup.17, N(R.sup.16)CON(R.sup.17)(R.sup.18), N.sub.3 or NH(C.sub.1 -C.sub.5 alkyl) substituted by one or more OH, OR.sup.14, S(O).sub.p R.sup.14, CN, NO.sub.2, COOR.sup.14 or CON(R.sup.16)(R.sup.17); SR.sup.14 and R.sup.14 ; ##STR6## R.sup.13 is H, halogen or R.sup.14 ; Ar is phenyl, optionally bearing one or more substituents selected from the group consisting of halogen, R.sup.15, OR.sup.15, SF.sub.5 and S(O).sub.p R.sup.15 ; or Ar is 2-pyridyl, optionally bearing one or more substituents selected from the group consisting of halogen, R.sup.15, OR.sup.15, SF.sub.5 and S(O).sub.p R.sup.14 ; alkyl, C.sub.3 -C.sub.6 cycloalkyl, and C.sub.4 -C.sub.8 (cycloalkyl)alkyl, each of which is optionally substituted by one or more halogen; halogen; NO.sub.2, CN, CHO, R.sup.19, COR.sup.19, and COOR.sup.19 ; one or more halogen; and OSO.sub.2 R.sup.4-, ClO.sub.4.sup.-, OCOR.sup.4-, BF.sub.4.sup.-, SbF.sub.6.sup.-, SO.sub.3.sup.- or HSO.sub.4.sup.-, a phosphate anion or a hydrogenophosphate anion or other agriculturally acceptable anion.
The stereoisomers, e.g. diastereomers and optical isomers, having the Formula (I) or (II) are included in the invention as well.
Preferred compounds of the present invention include one or more of the following features: methyl or ethyl; and/or COR.sup.4, P(O).sub.

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Hatton et al, Chemical Abstracts, vol. 120 (1994), abstract No. 298625p.

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