Amidine compounds and their use as pesticides

Details Amidine compounds and their use as pesticides Amidine compounds and their use as pesticides

2001-03-28

2002-04-23

Richter, Johann (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S245000, C564S246000, C043S125000, C043S127000

Reexamination Certificate

active

06376710

ABSTRACT:

FILED OF INVENTION
The present invention relates to amidine compounds and their use as pesticides.
BACKGROUND OF THE INVENTION
Various pesticides have been used for the control of pests including harmful insects, acarines, and nematodes. There have been drastic changes in the control of pests, such as development of new control systems for labor-saving, necessity for paying attention to influences on the environment, and occurrence of resistance to chemical agents in the target pests. Accordingly, development of chemical agents with novel structure or mechanism of action has been eagerly desired. An objective of the present invention is to provide novel compounds having insecticidal, acaricidal, and nematocidal activity, as well as novel pesticides containing these compounds as active agents.
SUMMARY OF THE INVENTION
Under these circumstances, the present inventors have extensively studied. As a result, they have found that amidine compounds of formula I as depicted below have excellent pesticidal effects, i.e., insecticidal, acaricidal, and nematocidal activity, thereby completing the present invention.
Thus the present invention provides amidine compounds of formula I (hereinafter referred to as the present compound(s)):
wherein X and Y are the same or different and are independently halogen, nitro, cyano, or C
1
-C
6
alkyl; Z is C
1
-C
6
haloalkyl or C
1
-C
6
haloalkoxy; R
1
is hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, or a group of formula: S(O)
n
—R
5
(wherein R
5
is C
1
-C
6
alkyl or C
1
-C
6
haloalkyl; and n is 0, 1, or 2); R
2
and R
3
are the same or different and are independently halogen or C
1
-C
6
haloalkyl; and R
4
is a group of formula: NR
6
R
7
or N═CR
8
R
9
(wherein R
6
is hydrogen, C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)-carbonyl, (C
1
-C
6
alkoxy) C
1
-C
6
alkyl, or C
2
-C
6
acyl; R
7
is hydrogen, C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl, or C
2
-C
6
acyl; R
8
is C
1
-C
6
alkyl or hydrogen; and R
9
is C
1
-C
6
alkoxy, C
1
-C
6
alkyl, or di(C
1
-C
6
alkyl)amino); and pesticides containing these amidine compounds as active ingredients.
DETAILED DESCRIPTION OF THE INVENTION
Specific examples of the substituents in the present compounds are as follows.
The “halogen” may include fluorine, chlorine, and bromine atoms.
The “C
1
-C
6
alkyl” may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, and hexyl groups.
The “C
1
-C
6
haloalkyl” may include trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, bromodifluoromethyl, dibromofluoromethyl, chlorofluoromethyl, bromofluoromethyl, dichloromethyl, 2-chlorotetrafluoroethyl, 2-bromotetrafluoroethyl, and 2,2,2-trifluoroethyl groups.
The “C
1
-C
6
haloalkoxy” may include trifluoromethoxy, pentafluoroethoxy, and difluoromethoxy groups.
The “(C
1
-C
6
alkoxy)carbonyl” may include methoxycarbonyl and ethoxycarbonyl groups.
The “(C
1
-C
6
alkoxy) C
1
-C
6
alkyl” may include methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, isobutoxymethyl, 2-methoxyethyl, 1-methoxy-2,2-dimethylpropyl, 1-ethoxy-2,2-dimethylpropyl, 1-methoxy-1,2,2-trimethylpropyl and 1-ethoxy-1,2,2-trimethylpropyl groups.
The “C
2
-C
6
acyl”, referring also to (C
1
-C
5
alkyl)carbonyl, may include acetyl, propanoyl, butanoyl, 3-methylbutanoyl, 2-methylpropanoyl, and pentanoyl groups.
The “C
1
-C
6
alkoxy” may include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, and tert-butoxy groups.
The “di(C
1
-C
6
alkyl)amino” may include dimethylamino, ethyl(methyl)amino, diethylamino, and dipropylamino groups.
Preferred substituents in the present compounds from the viewpoints of high insecticidal and acaricidal activity are as follows:
Each of X and Y may preferably be a halogen atom or a nitro group;
Z may preferably be a C
1
-C
6
haloalkyl group, specifically a trifluoromethyl group;
R
1
may preferably be a C
1
-C
6
haloalkyl group;
Each of R
2
and R
3
may preferably be a halogen atom;
R
4
may preferably be an amino group.
The following will describe some production processes for the present compounds. The present compounds can be produced, for example, by one of production processes 1 to 5 as described below.
Production Process 1
The present compounds wherein R
4
is a group of formula: NR
6
R
7
can be produced by reacting a compound of formula II:
wherein X, Y, Z, R
1
, R
2
, and R
3
are as defined above; and R
10
is halogen (e.g., chlorine, bromine, iodine), with a compound of formula III:
wherein R
6
and R
7
are as defined above, or a salt thereof in the presence of a base without any solvent or in a solvent.
The reaction is usually carried out at a temperature of about −5° C. to 150° C. for 1 minute to 24 hours. The amounts of reagents to be used in the reaction are usually 1 to 10 moles of compound III or a salt thereof and 1 to 10 moles of a base, relative to 1 mole of compound II. When compound III is allowed to act by itself as a base, this compound may be used in an amount of 2 mole to an excessive amount.
The base may include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; and tertiary amines such as triethylamine.
The solvent which can be used in the reaction may include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether; aromatic hydrocarbons such as toluene; halogenated hydrocarbons such as dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl acetate and butyl acetate; nitrites such as acetonitrile and isobutyronitrile; nitro compounds such as nitroethane and nitrobenzene; acid amides such as formamide, N,N-dimethylformamide, and N,N-dimethylacetamide; sulfur compounds such as dimethylsulfoxide and sulforane; water; and mixtures thereof.
After completion of the reaction, the reaction mixture is poured into water, followed by post-treatment including, for example, extraction with an organic solvent and evaporation of the organic layer, to give a product of the desired present compound. The product may be purified by chromatography, recrystallization, or any other technique.
Compound II can be produced by reacting a compound of formula IV:
wherein X, Y, Z, R
1
, R
2
, and R
3
are as defined above, with a halogenating agent according to the known methods (see, e.g., JP-A 8-295663).
The halogenating agent may include phosphorus pentachloride, phosphorus oxychloride, and triphenylphosphine-carbon tetrachloride.
The reaction is usually carried out at a temperature of about −5° C. to 150° C. for 1 to 24 hours. The amounts of reagents to be used in the reaction are 1 mole to an excessive amount of a halogenating agent, relative to 1 mole of compound IV.
The solvent which can be used in the reaction may include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether; aromatic hydrocarbons such as toluene; halogenated hydrocarbons such as dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.
After completion of the reaction, the reaction mixture is poured into water, followed by post-treatment including, for example, extraction with an organic solvent and evaporation of the organic layer, to give a product of the desired compound II. The product may be purified by chromatography, recrystallization, or any other technique.
Compound IV can be produced as shown in the following scheme:
wherein X, Y, Z, R
1
, R
2
, R
3
,

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