Pyridyl oxycarboxylic acid oxime derivative and preparation method therefor, weeding composition and application thereof
The invention relates to the field of pesticide technology, and in particular a type of pyridyloxy carboxylic oxime derivative, preparation method, herbicidal composition and application thereof. The pyridyloxy carboxylic oxime derivative is represented by formula I, wherein, A, B each independently represent halogen, or alkyl or cycloalkyl with or without halogen; C represents hydrogen, halogen, alkyl or haloalkyl; Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro, formyl, alkyl with or without halogen and the like; R 1 and R 2 independently represent hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio, or unsubstituted or substituted aryl, etc.; M represents nitro or NR 3 R 4 . The compound has excellent herbicidal activity and higher crop safety, especially good selectivity for key crops such as rice.
1 . A pyridyloxy carboxylic oxime derivative compound represented by formula I,
wherein the compound represented by formula I is selected from:
No.
A
B
C
Q
1
F
F
F
CH 3
2
Cl
Cl
Cl
CH 3
3
Cl
Cl
H
CH 3
4
Cl
Cl
F
CH 3
5
Cl
Cl
CH 3
CH 3
6
Cl
Cl
CF 3
CH 3
7
CH 3
CH 3
F
CH 3
8
Et
Et
CF 3
CH 3
9
Cl
H
CH 3
10
Cl
Cl
CH 3
11
F
CF 3
CH 3
12
Br
Br
F
CH 3
13
I
I
H
CH 3
14
F
CH 3
15
CF 3
Cl
F
CH 3
16
Cl
CF 3
H
CH 3
17
Cl
Cl
I
CH 3
18
Cl
Br
CH 3
19
CH 3
CH 3
CH 3
CH 3
20
Cl
CH 3
F
CH 3
21
Cl
CH 3
H
CH 3
22
Cl
F
CH 3
23
Cl
Cl
H
CH 3
24
Cl
Cl
Cl
CH 3
25
Cl
Cl
F
Et
26
Cl
Cl
F
27
Cl
Cl
F
28
Cl
Cl
F
29
Cl
Cl
F
30
Cl
Cl
F
31
Cl
Cl
F
32
Cl
Cl
F
33
Cl
Cl
F
34
Cl
Cl
F
F
35
Cl
Cl
F
Cl
36
Cl
Cl
F
Br
37
Cl
Cl
F
38
Cl
Cl
F
39
Cl
Cl
F
40
Cl
Cl
F
41
Cl
Cl
F
CF 3
42
Cl
Cl
F
43
Cl
Cl
F
CN
44
Cl
Cl
F
45
Cl
Cl
F
NH 2
46
Cl
Cl
F
47
Cl
Cl
F
48
Cl
Cl
F
49
Cl
Cl
F
NO 2
50
Cl
Cl
F
51
Cl
Cl
F
52
Cl
Cl
F
53
Cl
Cl
F
54
Cl
Cl
F
55
Cl
Cl
F
56
Cl
Cl
F
57
Cl
Cl
F
58
Cl
Cl
F
59
Cl
Cl
F
60
Cl
Cl
F
61
Cl
Cl
F
62
Cl
Cl
F
63
Cl
Cl
F
64
Cl
Cl
F
65
Cl
Cl
F
66
Cl
Cl
F
67
Cl
Cl
F
CH 3
68
Cl
Cl
F
CH 3
69
Cl
Cl
F
CH 3
70
Cl
Cl
F
CH 3
71
Cl
Cl
F
CH 3
72
Cl
Cl
F
CH 3
73
Cl
Cl
F
CH 3
74
Cl
Cl
F
CH 3
75
Cl
Cl
F
CH 3
76
Cl
Cl
F
CH 3
77
Cl
Cl
F
CH 3
78
Cl
Cl
F
CH 3
79
Cl
Cl
F
CH 3
80
Cl
Cl
F
CH 3
81
Cl
Cl
F
CH 3
82
Cl
Cl
F
CH 3
83
Cl
Cl
F
CH 3
84
Cl
Cl
F
CH 3
85
Cl
Cl
F
CH 3
86
Cl
Cl
F
CH 3
87
Cl
Cl
F
CH 3
88
Cl
Cl
F
CH 3
89
Cl
Cl
F
CH 3
90
Cl
Cl
F
CH 3
91
Cl
Cl
F
CH 3
92
Cl
Cl
F
CH 3
93
Cl
Cl
F
CH 3
94
Cl
Cl
F
CH 3
95
Cl
Cl
F
CH 3
96
Cl
Cl
F
CH 3
97
Cl
Cl
F
CH 3
98
Cl
Cl
F
CH 3
99
Cl
Cl
F
CH 3
100
Cl
Cl
F
CH 3
101
Cl
Cl
F
CH 3
102
Cl
Cl
F
CH 3
103
Cl
Cl
F
CH 3
104
Cl
Cl
F
CH 3
105
Cl
Cl
F
CH 3
106
Cl
Cl
F
CH 3
107
Cl
Cl
F
CH 3
108
Cl
Cl
F
CH 3
109
Cl
Cl
F
CH 3
110
Cl
Cl
F
CH 3
111
Cl
Cl
F
CH 3
112
Cl
Cl
F
CH 3
113
Cl
Cl
F
CH 3
114
Cl
Cl
F
CH 3
115
Cl
Cl
F
CH 3
116
Cl
Cl
F
CH 3
117
Cl
Cl
F
CH 3
118
Cl
Cl
F
CH 3
No.
R 1
R 2
M
1
Me
Me
NH 2
2
Me
Ph
NH 2
3
Ph
Ph
NH 2
4
Me
Ph
NH 2
5
Me
Ph
NH 2
6
Me
Ph
NH 2
7
Me
Ph
NH 2
8
Me
Ph
NH 2
9
Ph
Ph
NH 2
10
Me
Ph
NH 2
11
Me
Ph
NH 2
12
Me
Ph
NH 2
13
Ph
Ph
NH 2
14
Me
Ph
NH 2
15
Me
Me
NH 2
16
Me
Me
NH 2
17
Me
—CH(CH 3 ) 2
NH 2
18
Ph
Ph
NH 2
19
Me
CH 2 CH 2 Cl
NH 2
20
Me
Me
NH 2
21
Me
Me
NH 2
22
Me
Me
NH 2
23
Me
Me
NH 2
24
Me
Me
NH 2
25
Me
Ph
NH 2
26
Me
Ph
NH 2
27
Me
Et
NH 2
28
Me
—CH 2 CH 2 CH 3
NH 2
29
Ph
Ph
NH 2
30
Me
Ph
NH 2
31
Me
—C(CH 3 ) 3
NH 2
32
Me
Me
NH 2
33
Me
Me
NH 2
34
Me
Me
NH 2
35
Me
Me
NH 2
36
Me
Me
NH 2
37
Me
Me
NH 2
38
Me
Me
NH 2
39
Me
Me
NH 2
40
Me
Me
NH 2
41
Me
Me
NH 2
42
Me
Me
NH 2
43
Me
Me
NH 2
44
Me
Me
NH 2
45
Me
Me
NH 2
46
Me
Me
NH 2
47
Me
Me
NH 2
48
Me
Me
NH 2
49
Me
Me
NH 2
50
Me
Me
NH 2
51
Me
Me
NH 2
52
Me
Me
NH 2
53
Me
Me
NH 2
54
Me
Me
NH 2
55
Me
Me
NH 2
56
Me
Me
NH 2
57
Me
Me
NH 2
58
Me
Me
NH 2
59
Me
Me
NH 2
60
Me
Ph
NH 2
61
Me
OEt
NH 2
62
H
H
NH 2
63
H
Et
NH 2
64
Me
Me
NH 2
65
Me
Me
NH 2
66
Et
Et
NH 2
67
Me
Me
NH 2
68
Et
—CH(CH 3 ) 2
NH 2
69
Et
n-Bu
NH 2
70
Me
4-
NH 2
Cl, Ph
71
Me
4-
NH 2
NO 2 , Ph
72
H
Ph
NH 2
73
H
3-
NH 2
NO 2 , Ph
74
Et
Ph
NH 2
75
CH 2 CH 2 CH 3
Cl
NH 2
76
n-Bu
OEt
NH 2
77
Ph
NH 2
78
Ph
Ph
NH 2
79
Ph
3-Cl, Ph
NH 2
80
Ph
4-
Ph
NH 2
81
4-CF 3 , Ph
Ph
NH 2
82
3-F, Ph
4-Cl, Ph
NH 2
83
4-F, Ph
Ph
NH 2
84
F
2-
NH 2
OMe, Ph
85
Cl
3-
NH 2
Et, Ph
86
Br
4-
NH 2
CN, Ph
87
CN
4-Cl, Ph
NH 2
88
OEt
4-
NH 2
NHCOMe,
Ph
89
SMe
4-
NH 2
SMe, Ph
90
NO 2
4-N(Me) 2 ,
NH 2
Ph
91
Ac
4-
NH 2
NHOPh, Ph
92
COOEt
4-
Ph
NH 2
93
Bn
2-
NH 2
NH 2 , Ph
94
CONHBn
NH 2
95
NH 2
96
OPh
COOPh
NH 2
97
SPh
COEt
NH 2
98
CONHPr
Ph
NH 2
99
CON(Me) 2
Ph
NH 2
100
Et
NH 2
101
Ph
NH 2
102
COSMe
NH 2
103
Me
NH 2
104
Ph
NH 2
105
Ph
NH 2
106
CONMePh
NH 2
107
Ph
NH 2
108
Et
NH 2
109
COOMe
NH 2
110
CH 3
CH 3
111
CH 3
CH 3
112
CH 3
CH 3
113
CH 3
CH 3
114
CH 3
CH 3
115
CH 3
CH 3
116
NH 2
represents
117
NH 2
represents
118
CH 3
CH 3
2 . A method of preparing the pyridyloxy carboxylic oxime derivative according to claim 1 , comprising:
reacting a compound of formula II with a compound of formula III to obtain a compound of formula I as follows:
3 . The method of claim 2 , wherein the reaction is carried out in the presence of a dehydrant and a solvent.
4 . The method of claim 3 , wherein the dehydrant is DCC, and the solvent is one or more solvent selected from the group consisting of dichloromethane, dichloroethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene.
5 . A herbicidal composition, comprising (i) at least one pyridyloxy carboxylic oxime derivative of claim 1 ; optionally further comprising (ii) at least one additional herbicide and/or safener, and/or (iii) at least one agrochemically acceptable formulation auxiliary.
6 . A method for controlling a weed, comprising applying a herbicidally effective amount of at least one pyridyloxy carboxylic oxime derivative of claim 1 on a plant or in a weed area.
7 . The method of claim 6 , wherein the plant is rice; or the weed is a gramineous weed, a broad-leaved weed, or a cyperaceae weed.
8 . The method of claim 6 , wherein the plant is japonica rice or indica rice; or the weed is Digitaria sanguinalis, Echinochlca crusgalli, Setaria viridis, Leptochloa chinensis, Monochoria Vaginalis, Galium spurium, Sagittaria trifolia, Murdannia triquetra, Cyperus iria , or Scirpus juncoides.
9 . A method for controlling a weed in a useful crop, comprising applying at least one pyridyloxy carboxylic oxime derivative of claim 1 to the useful crop or in a weed area.
10 . The method of claim 8 , wherein the useful crop is a genetically modified crop, or a crop treated by gene editing technology.
11 . The method of claim 9 , wherein the useful crop is rice; or the weed is a gramineous weed, a broad-leaved weed, or a cryperaceae weed.
12 . The method of claim 9 , wherein the useful crop is japonica rice or indica rice; or the weed is Digitaria sanguinalis, Echinochloa crusgalli, Setaria viridis, Leptochloa chinensis, Monochoria Vaginalis, Galium spurium, Sagittaria trifolia, Murdannia triquetra, Cyperus iria , or Scirpus juncoides.