Pesticidal 1-polyarylpyrazoles

Details Pesticidal 1-polyarylpyrazoles Pesticidal 1-polyarylpyrazoles

2001-07-13

2002-12-10

Ramsuer, Robert W. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S404000, C514S407000

Reissue Patent

active

RE037936

ABSTRACT:

The invention relates to new 1-arylpyrazoles and derivatives thereof which have some valuable properties either as pesticides or as intermediates to make other pesticides. The invention further pertains to compositions of said compounds and methods, using said compounds either as intermediates to make other pesticides, or for the control of pests particularly insects, in particular to the application of said compounds or compositions in agricultural methods of use or for animal protection, particularly as pesticides, for controlling arthropods.
International Patent Publication No. WO 87/03781 and European Patent Publication No. 295117, 154115, 201852 describe insecticidal 1-(substituted phenyl)pyrazoles. Other prior art is also found in the text of these patent applications or the patents issued therefrom.
International Patent Publications No. WO 93/06089 and WO 94/21606 also describe insecticidal 1-(4-SF
5
substituted phenyl) heterocycles which may be pyrroles as well as imidazoles or pyrazoles. The teaching of these patents is not substantially different from International Patent Publication No. WO 87/03781 or from European Patent Publication No. 0295117 as far as pyrazoles are concerned.
It is an object of the present invention to provide new pesticidal compounds of the 1-arylpyrazole family together with processes for their preparation.
Another object of the present invention is to provide pesticidal compositions and pesticidal methods of use of the pesticidal pyrazole compounds against arthropods, especially insects, particularly in agricultural or horticultural crops, forestry, veterinary medicine or livestock husbandry, or in public health.
A third object of the present invention is to provide very active compounds with broad spectrum pesticidal activity, as well as compounds with selective special activity, e.g., aphicidal, miticidal, foliar insecticidal, soil insecticidal, systemic, antifeeding or pesticidal activity via seed treatment.
A fourth object of the present invention is to provide compounds with substantially enhanced and more rapid activity, especially against insects and more particularly insects in their larval stages.
A fifth objective of the present invention is to provide compounds with greatly improved (faster and greater) penetration into pest species when topically applied and to thus provide enhanced movement of the compounds to the pesticidal site(s) of action within the pest.
These and other objectives of the invention are met in whole or part and shall become readily apparent from the description of the present invention which follows.
The invention thus relates to compounds having the general formula (I):
wherein
X is N or C—R
2
;
Y is N or C—R
3
;
W is N or C—R
4
;
R
2
and R
3
are independently selected from H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO
2
, —S(O)
n
R
8
, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, and dialkylaminosulfonyl;
R
4
is H, halogen, alkyl, alkoxy, CN, NO
2
, haloalkyl, haloalkoxy, thiocyanato, formyl, alkylcarbonyl, —CH═N—OH,
—CH═N—O-alkyl.

—CH═N—O-alkyl,
—S(NH
2
)(═NH), —S(O)
n
R
8
, mercapto, haloalkylcarbonyl, or a —S—radical so that two molecules are bound together to form a disulfide compound;
R
5
is hydrogen, halogen, —NR
9
R
10
, —N═CR
11
R
19
, —S(O)
n
R
8
, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkylthiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl;
R
8
is alkyl or haloalkyl, alkenyl or alkynyl, or a cycloalkyl ring containing 3 to 5 carbon atoms;
R
11
is H, or alkyl;
R
19
may also be hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, dialkylamino, or R
19
is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with alkyl, haloalkyl, halogen, NO
2
, CN, alkoxy, haloalkoxy, OH, alkylcarbonyl, alkylcarbonyloxy;
R
9
and R
10
independent of one another, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R
8
S(O)
n
, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, aroyl; or are joined so as together form a divalent radical having 4 to 6 atoms in the chain, this divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, preferably to form a morpholine, pyrrolidine, piperidine or piperazine ring; the alkyl portion of R
9
and R
10
may be substituted by R
7
;
R
7
is cyano, nitro, alkoxy, haloalkoxy, R
8
S(O)
n
, —C(O) alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO
2
H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
Z is N or C—R
16
;
n is zero, one or two;
R
12
, R
13
, R
15
, R
16
, are independently selected from hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl, alkoxycarbonyl;
R
22
, R
23
, R
24
, R
25
, R
26
are
hydrogen,
halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, and alkoxycarbonyl, SF
5
, R
8
S(O)
n
; preferably R
24
is halogen, haloalkyl or haloalkoxy; or R
22
and R
23
or R
23
and R
24
or R
25
and R
26
may also be together a divinylidene group (—CH═CH—CH═CH—) or a methylene diether (—O—CH
2
—O—) or halomethylene diether (—O—CF
2
—O—), so as to form a cyclic ring vicinal to the phenyl ring; or pesticidally acceptable salts thereof.
By the term “pesticidally acceptable salts” is meant salts the anions and cations of which are known and accepted in the art for the formation of pesticidally acceptable salts. Preferably such salts are water soluble. Suitable acid addition salts formed from compounds of formula (I) containing an amine group, include salts with inorganic acids for example hydrochlorides, phosphates, sulfates and nitrates, and salts with organic acids for example acetates. Suitable salts with bases formed from compounds of formula (I) containing a suitably acidic group include alkali metal (for example sodium or potassium) salts, ammonium salts and organic amine (for example diethanolamine or morpholine) salts.
In the present invention, some words are used in a specific sense:
The term “lower alkyl-S(O)
n
” means a radical of the formula —S(O)
n
— lower alkyl. The term “R
10
S(O)
n
” means a radical of the formula —S(O)
n
R
10
. The term “aminocarbonyl” means a carbamoyl radical, that is, a radical of the formula —C(O)NH
2
. Similarly, the term “alkylaminocarbonyl” means an
alkylcarbomoyl

alkylcarbamoyl
radical, that is, a radical of the formula —C(O)—NH-alkyl; and the term “dialkylaminocarbonyl” means a dialkylcarbamoyl radical, that is, a radical of the formula —C(O)—N(alkyl)
2
in which the alkyl moieties can be the same or different. The term “aminosulfonyl” means a sulfamoyl radical, that is, —SO
2
NH
2
. Similarly, the term “alkylaminosulfonyl” means an alkylsulfamoyl radical, that is, a radical of the formula —SO
2
NH-alkyl; while the term “dialkylaminosulfonyl” means a dialkylsulfamoyl radical, which has the formula —SO
2
N(alkyl)
2
wherein the alkyl moieties can be the same or different.
The term “halo” before the name of a radical means that this radical is partially or completely halogenated, that is to say, substituted by F, Cl, Br, or I, in any combination, preferably by F or Cl. The term “halogen” means F, Cl, Br or I. The term “lower” before the name of a radical having a carbon skeleton means that this carbon skeleton has less than 6 carbon atoms. When the name of any substituent is repeated, it keeps the same meaning unless otherwise specified. The term “aryl” designates a carbon and/or heteroatom-containing aromatic radical which is preferably phenyl optionally substituted with one or more substituents selected from halogen, methyl and methoxy, especially phenyl, halophenyl, tolyl or xylyl. The

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