2-Pyrimidinyloxy-n-aryl-benzylamine derivatives,their...

Details 2-Pyrimidinyloxy-n-aryl-benzylamine derivatives,their... 2-Pyrimidinyloxy-n-aryl-benzylamine derivatives,their...

2003-04-09

2004-10-05

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S243000, C544S300000, C544S301000, C544S310000, C544S312000, C544S316000

Reexamination Certificate

active

06800590

ABSTRACT:

TECHNICAL FIELD
The present invention relates to new 2-pyrimidinyloxy-N-aryl-benzylamine derivatives, their preparation processes and uses as chemical herbicides in agriculture.
BACKGROUND ART
Agricultural chemicals are the indispensable productive materials for human to obtain provisions, to stably produce grain mass with good harvest. In recent hundred years, agricultural chemicals such as insecticides, bactericides, herbicides and the like made a great contribution to human beings. Recently, as the population of the world continues growing, the need of people to provisions is continuously increasing. However, the increasing rate of plowland can not be kept with the growing rate of population. In order to solve the cosmopolitan problem, we must rely on increasing crop yield per unit area and improving the quality of crops. It is necessary to apply various means such as breeding, arable farming, fertilizing and the like. Of those, the use of agricultural chemicals is an essential one of these means. However, it should also be seen that while agricultural chemicals made a great contribution to human civilization, high toxic, high residual agricultural chemicals also bring along negative effect on the environment which human beings rely on because of the knowledge limitation of human to agricultural chemicals. It is the direction of developing new agricultural chemicals to develop high efficient, low toxic, degradable, safe and environmental friendly agricultural chemicals instead of those low efficient, high toxic, high residual and high resistant ones.
It is reported in references that pyrimidinyloxy benzene derivatives can be used as chemical herbicides, for example, in Agr. Biol. Chem., vol. 30, p 896 (1966), JP 79-55729, U.S. Pat. Nos. 4,248,619 and 4,427,437. Recently, on the basis of pyrimidinyloxy benzene derivatives, a class of compound with excellent weeding activity, pyrimidine salicylic acid derivatives, is found, such as in EP 223,406; 249,708; 287,072; 287,079; 315,889; 321,846; 330,990; 335,409; 346,789; 363,040; 402,751; 435,170; 435,186; 457,505; 459,243; 468,690; 658,549 and 768,034; JP 04368361; GB 2,237,570; DE 3,942,476, etc. Of those, the representative examples are Pyrithiobac-sodium (KIH-2031, EP 315,889), Bispyribac-sodium (KIH-2023, EP 321,846), Pyriminobac-methyl (KIH-6127, JP 04,368,361), Pyribenzoxim (EP 658549) and Pyriftalid (EP 768,034). The action mechanism thereof is the same as that of sulfonyl urea herbicides, both of them are inhibitors of acetyl lactic acid synthetase (ALS), destroying the synthesis of amino acid such as valine, leucine and isoleucine within plant bodies. Although pyrimidine salicylic acid derivatives have very high weed control activity, currently they are only suitable to weed control in cotton field and paddy field.
OBJECTIVES OF THE PRESENT INVENTION
An objective of the present invention is to provide a 2-pyrimidinyloxy-N-aryl-benzylamine derivative.
Another objective of the present invention is to provide a process for preparing 2-pyrimidinyloxy-N-aryl-benzylamine derivative.
One further objective of the present invention is to provide the use of 2-pyrimidinyloxy-N-aryl-benzylamine derivative as an effective active ingredient in herbicides.
SUMMARY OF THE PRESENT INVENTION
The present invention relates to a 2-pyrimidinyloxy-N-aryl-benzylamine derivative. One target compound, 2-pyrimidinyloxy-N-aryl-benzylamine, is prepared in the following way: firstly, reacting salicylal with an aromatic amine to produce intermediate (II), secondly, reducing the intermediate (II) to afford the corresponding intermediate (III), and finally, further reacting the intermediate (III) with 2-methylsulfonyl (i.e.CH
3
SO
2
-)-4D,6E-substituted pyrimidine in the present of a base to produce the target compound. The reaction between the target compound and an acid anhydride or acid chloride compound in the presence of a base can produce another target product, i.e., N-acylated product of 2-pyrimidinyloxy-N-aryl-benzylamine. The compound of the present invention is an active ingredient in herbicides, which can be formulated into various liquor, oil solutions, emulsions, powder preparations, granule preparations or capsule preparations, etc. and applied to weed control of crops such as rape, cotton, paddy, soybean and the like.
DISCLOSURE OF THE INVENTION
The 2-pyrimidinyloxy-N-aryl-benzylamine derivatives of the present invention are represented by the following structure (I):
where:
D and E can be same or different, and each independently represents hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl or C
1
-C
4
haloalkoxy, particularly both of D and E are methoxy.
R
1
is hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, which can be at any one position of 3-, 4-, 5-, 6-positons in benzene ring.
R
2
is hydrogen; halogen; C
1
-C
4
alkyl; C
1
-C
4
alkoxy; C
1
-C
4
carbamyl; C
1
-C
4
alkoxycarbonyl; C
1
-C
4
haloalkyl, particularly trifluoromethyl; cyano; nitro; carboxy or its alkali metal, alkali earth metal and organoammonium salts; C
1
-C
4
alkylamido; C
1
-C
4
haloalkylamido, particularly trifluoromethylamido; benzamido or substituted benzamido (substituents can be halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, trifluoromethyl, cyano, nitro, etc. located at m-, o- or p-position); heterocyclic amido, such as, for example, pyridine, thiophene, thiazole, pyrimidine, etc; R
2
can be located at m-, o- or p-position of a benzene ring (n=1-3), or be a benzo or substituted benzo compound, preferably, R
2
is a halogen monosubstituting at m-, o- or p-position of a benzene ring; methyl; methoxy; trifluoromethyl; C
1
-C
4
alkoxycarbonyl; C
1
-C
4
carbamyl; carboxy or its sodium, potassium or ammonium salts; C
1
-C
4
alkylamido; benzamido or substituted benzamido; heterocyclic amido and the like.
R
3
is hydrogen, C
1
-C
4
alkanoyl, C
1
-C
4
haloalkanoyl, benzoyl and C
1
-C
4
alkoxyacetyl. R
3
is preferably being hydrogen, acetyl, chloroacetyl, dichloroacetyl, benzoyl or methoxyacetyl, particularly hydrogen.
X is H or N, preferably H.
Next, the typical compounds the present invention involves are listed in Table 1.
TABLE 1
2-pyrimidinyloxy-N-aryl-benzylamine derivatives
Compound No.
D═E
R
1
R
3
X
I-1
OCH
3
H
H
H
H
I-2
OCH
3
6-Cl
H
H
H
I-3
OCH
3
5-F
H
H
H
I-4
OCH
3
5-OCH
3
H
H
H
I-5
OCH
3
5-Cl
H
H
H
I-6
OCH
3
H
2-F
H
H
I-7
OCH
3
H
2-F
—COCH
2
OCH
3
H
I-8
OCH
3
H
2-F
—COCH
2
Cl
H
I-9
OCH
3
H
3-F
—COCH
2
Cl
H
I-10
OCH
3
6-Cl
4-F
H
H
I-11
OCH
3
H
2-Cl
H
H
I-12
OCH
3
H
2-Cl
—COCH
2
Cl
H
I-13
OCH
3
H
3-Cl
H
H
I-14
OCH
3
H
3-Cl
—COCH
2
Cl
H
I-15
OCH
3
H
3-Cl
—COCH
2
OCH
3
H
I-16
OCH
3
H
4-Cl
H
H
I-17
OCH
3
H
4-Cl
—COCH
2
Cl
H
I-18
OCH
3
H
4-Cl
—COCH
2
OCH
3
H
I-19
OCH
3
3-OCH
3
2-Br
H
H
I-20
OCH
3
H
4-Br
H
H
I-21
OCH
3
H
4-Br
—CO(CH
2
)
3
Cl
H
I-22
OCH
3
H
4-Br
—CO(C
6
H
5
)
H
I-23
OCH
3
H
4-Br
—COCHCl
2
H
I-24
OCH
3
H
4-Br
—COCH
2
CH
3
H
I-25
OCH
3
H
4-Br
—COCHCl
2
H
I-26
OCH
3
H
2-I
H
H
I-27
OCH
3
H
2-I
—COCH
2
Cl
H
I-28
OCH
3
H
3-I
H
H
I-29
OCH
3
H
3-I
—COCH
2
Cl
H
I-30
OCH
3
H
3-I
—COCH
2
OCH
3
H
I-31
OCH
3
H
4-I
H
H
I-32
OCH
3
H
4-I
—COCH
2
Cl
H
I-33
OCH
3
H
4-I
—COCHCl
2
H
I-34
OCH
3
H
4-I
—COCH
3
H
I-35
OCH
3
H
4-I
—COCH
2
OCH
3
H
I-36
OCH
3
H
2-CH
3
H
H
I-37
OCH
3
H
2-CH
3
—COCH
2
Cl
H
I-38
OCH
3
H
4-CH
3
H
H
I-39
OCH
3
H
4-CH
3
—COCH
2
Cl
H
I-40
OCH
3
H
2-CF
3
H
H
I-41
OCH
3
H
2-CF
3
—COCH
2
Cl
H
I-42
OCH
3
H
4-CF
3
H
H
I-43
OCH
3
H
4-CF
3
—COCH
2
Cl
H
I-44
OCH
3
H
4-OCH
3
H
H
I-45
OCH
3
H
4-OCH
3
—COCHCl
2
H
I-46
OCH
3
H
4-OCH
3
—CO(CH
2
)
3
Cl
H
I-47
OCH
3
H
3,4-di-F
H
H
I-48
OCH
3
H
2,5-di-Cl
H
H
I-49
OCH
3
H
2,5-di-Cl
—COCH
2
Cl
H
I-50
OCH
3
H
2,3-di-Cl
H
H
I-51
OCH
3
H
2,3-di-Cl
—COCH
2
Cl
H
I-52
OCH
3
H
3,4-di-Cl
H
H
I-53
OCH
3
H
3,4-di-Cl
—COCH
2
Cl
H
I-54
OCH
3
H
3,4-di-Cl
—COCH
2
OCH
3
H
I-55
OCH
3
3-OCH
3
3,4-di-Cl
H
H
I-56
OCH
3
H
3,5-di-Cl
H
H
I-57
OCH
3
H
3,5-di-Cl
—COCH
2
Cl
H
I-58
OCH
3
H
2,4-di-Cl
H
H
I-59
OCH
3
H
2,4-di-Cl
—COCH
2
Cl
H
I-60
OCH
3
H
2,4-di-Cl-3-F
H
H
I-61
OCH
3
3-OCH
3
2,4-di-Cl-3-F
H
H
I-62
OCH
3
H
2-F-4-Br
H
H
I-63
OCH
3
3-OCH
3
2-F-4-Br
H
H
I-64
OCH
3
H
2-CH
3
-5-

Affiliated with

Also associated with

Rating

2-Pyrimidinyloxy-n-aryl-benzylamine derivatives,their... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-Pyrimidinyloxy-n-aryl-benzylamine derivatives,their..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-Pyrimidinyloxy-n-aryl-benzylamine derivatives,their... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3259252