JPS6087238A - 2-(2-substituted benzoyl)-1,3-cyclohexandione - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The compound () having the following formula (wherein where R1, X and n are the same as above), Rs is alkyl, and alkenyl is alkynyl. The herbicidal compounds specifically indicated are n
is 2, X is 5,5-methyl, R1 is allyl, J+'!
phenyl, 4-chlorophenylal or 4-methoxyphenyl.

The precursor intermediates of these three particularly indicated compounds have almost no herbicidal activity.

In contrast, the compounds of the present invention have excellent herbicidal activity. The compound must have a chlorine, bromine, iodine or alkoxy substitution at the 2-position of its phenyl moiety in order to have herbicidal activity. Chlorine is a preferred substituent. The reasons why such substituents confer superior herbicidal activity are not fully understood.

This invention discloses novel 2- (2-
[benzoyl]-cyclohexane-1,3-phono. The compound of the present invention has the following structural formula.

Here, R and R1 are hydrogen, C alkyl, preferably 1-4, preferably methyl, isopropyl, ROC(C)-, and R is C0-4 alkyl: most preferably R and R1 are hydrogen; R is chlorine, bromine, iodine or C a1-4 alkoxy, preferably methoxy; most preferably R8 is chlorine, bromine or methoxy.

8 B4 and R1 are independently hydrogen or an aliphatic group; preferably: (1) hydrogen; (2) halogen, preferably chlorine or bromine; (3) 01-4 alkyl, preferably methyl; (4) C alkoxy 1-4, preferably methoxy: (5) 0CFs; (
6) Cyano; (7) Two-handed; (8) 01-4 haloalkyl, more preferably trifluoromethyl 1(9)R
8O-1 where Rb is C1-4 alkyl, preferably methyl, Ce haloalkyl, phenyl, benzyl, -NRR.

e where R and R are independently hydrogen or Ca1-4 f R,C(0), where R is hydrogen, C alkyl, 1-4 C haloalkyl, C alkoxy; (12) 1-4 -NFL "Rh, where Rg and Rh are independently hydrogen or C1-4 alkyl; or (13) R" and R4
may form a ring structure with two adjacent carbon atoms of the enyl ring. Most preferably R8 is chlorine, hydrogen,
Dimethylamino, methoxy, preferably R4 is hydrogen, chlorine, nitro, So, CH.

5OIN(CHs)m or CFs% preferably R
1 is hydrogen.

The compounds of the present invention can be obtained by tautomerism υ where R,
R1, R", R", R4 and R are as described above.

The protons circled in each of the four tautomers are easily mutable. These protons are removed by acid and base to form anions with the following four types of resonance structures.

Coconi, R, R1, R", R", R'ojhi R'! !
As mentioned above.

Examples of these base cations are inorganic cations such as alkali metals such as lithium, sodium and potassium, alkaline earth metals such as barium, magnesium, calcium and strontium, and those in which the substituents are aliphatic or aromatic. Substituted ammonium, sulfonium, Jr
-P is an organic cation such as sulfonium.

The term "aliphatic group" used here is used in a broad sense, and includes (1
) acylic (open chain structure) of olefins and acetylenic hydrocarbons and their derivatives;
lic) represents a wide range of organic groups that can be obtained from compounds.

"Aromatic group" is used in a broad sense to distinguish it from aliphatic group, and (1) C has at least one 6 to 20 benzene ring, monocyclic, bicyclic, polycyclic. (2) A heterocyclic compound of C, containing at least one of nitrogen, sulfur, and oxygen in the case of 6 to 50 atoms other than carbon, and having an unsaturated ring structure. and derivatives thereof.

In the above description, both alkyl and alkoxy groups include straight chain and branched structures.

Examples include methyl, ethyl, n-propyl, isonorovir, n-butyl, 2-butyl, isobutyl, tert-butyl, and the like.

The compounds of the present invention and their salts have general types of herbicidal activity. That is, it has herbicidal activity against a wide range of plant species. The method of controlling unwanted plants according to the present invention is carried out by applying a herbicidally effective amount of the above compound to a location requiring plant control.

Compounds of the invention can be prepared by the following general method.

U@ Generally, equimolar amounts of dione and substituted benzoyl cyanide are used with a slight molar excess of zinc chloride. These are mixed in a solvent such as methylene chloride. Slowly add a slight excess of triethylamine to this while cooling.
Add. This is stirred at room temperature for 5 hours. The reaction products are worked up in the usual manner.

The above substituted benzoyl cyanide is
Written by Oakwood and C.E.
Organic Synthesis Collection (T, S, Oakwood.

C, A, Weisgerbs+r, OrganIc
5ynthes1s Co11ect -*d) Val
, nI, pp. 122 (1955).

The following examples demonstrate the synthesis of representative compounds of the invention.

(Example I) 1,3-cyclohexanedione (11,2 g, 0,1 mol), 2,4-dichlorobenzoyl cyanide (20
,0 g, 0.1 mol) and anhydrous powdered zinc chloride (13
,6!1.0.11 mol) to methylene chloride (10
0d) I put it inside. Triethylamine (10.1g, 0
．． 12 mol) was gradually added under cooling.

The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. Separate the aqueous phase and combine the organic phase with 150-55-N
Washed 4 times with a1CO solution. The aqueous washes were combined and acidified with Hα and extracted with methylene chloride. Concentrated and dried 25.3! A crude product of / was obtained. Dissolve the sample in ether and stir with 250% 5% cupric acetate solution.

The resulting copper salt is filtered, washed with ether, and stirred with 6N hydrochloric acid to decompose the salt. Wash the extract with ether to obtain 22.159 of the desired product. m, p, 1
The temperature was 38-140°C, and the yield was 77.7%.

The structure was confirmed by instrumental analysis (NMR, IR and mass spectrometry).

The following table is a table of compounds selected as preferred compounds. Each compound is numbered and used throughout this specification.

18 :HHα 3-α 19 HHα ■ 20HHα 3-α 21 HHα ■ 22HHα H 23HHα 3-α 24HHα 3-α 25HHα H 26CHs CHs CHsOH (21) ■ 6-α H5-CHso 77-80 HH8O-90 H5-CFs 74-75 H5-No! 140-143 4-α H152-154 4-CHsOH169-170 4-Br H104-107 HH104-108 Weak Sodium salt of compound 23 45 Inglovir of compound 23 46 Triethyla of compound 23 47 Potassium chloride of compound 23 Compound 390 Triethano- 49 Sodium salt of compound 43 50 CH(CHsh Hα 51HHCt 52 HCHs α 53 to(aHy Hα 54 j C3H6Hα H4-F' H 5-94 T Min salt 160-165 Min salt 82-85 107-106 r Reammonium salt 0-63 3-OCHx 4-Br H H4-CHsSOg H ■ 4-α H H4-α H 3-0CHs HH :22) Table I 55 CHg CHsαH 56CH3CH3α3-CH3 57HT(C13-CH3 58HHαH 59HHα3-O 60HHαH 61HHα3-OCHs 62 CHs CHsαH 63HHα3-α 64T(Hα3 C2H55 65CHs CH3αH 66CHs 'CHsα3-α 571-C4H7HαH 68HHα3-α 691-cslHy HC13-C1 70HHC1H 71HHCtH 72HHctH (continued) @) 4 CH35O2-H 4-Cl H 4-Cl H 4-Cd et al. S(h H98100 4-C2H5SO2-H' 98-1094-C stop rS
Ox-H semi-solid 4 CH3SO2H4859 4-n-CsHySOz H semi-solid 4-n-C3H75O2-H14514854-CzH
sSOz H oily 4-beam H5SO2H' 103 1084-C2HsS
Oz-H108111 4C2H55O2-' H brown gum 4-CHsS (h~ H145-1544-CHsSO
z H 4-CH5S(h H brown gum 4-i -C stop, SO, -H 4-CH5FEr-H7077 73H!(03-α 74 CHs CH3α 3-α 75HHCgH 76CR3CHs α H 77HHCl 3-0C2H5- 78I(Hα 3-0CH3 79CHs CHs α H *=Prepared in Example 1 (a) = 4-CH5C-NH- and (b) = 5(
23) 4-CHsS-H 4-C2H5SO2~ 120-1234-n-C4I
(@So□-H 4n-C4HsSO1H 4-CHsSOz H semisolid 4-n -CzHrSOz H golden gum 4-i-CsH
ySOz-H125128C) Herbicidal Effect Test As mentioned above, the compound prepared by the above method is a phytotoxic compound and is useful for controlling various plants. Selected compounds of the invention were tested for herbicidal efficacy in the following manner.

Prior to the pre-emergence test treatment, seeds of eight different weed species were planted in each row on the loamy sand of the test flat, one species per row. The seeds used were Green Foxtail (FT) (5etaria virldlg),
Water Glass (WG) (Echin*ahloa
erusgall amount), Annual Morning Glory (AMG) (Ip*moea lacunosm
)) Wild O) (W O) (Av+sna
fa engineering), velvet leaf (V L) (Abu
tllon then hrasti), Indian mustard (MD) (Bragsica Jun
-cea), red root pyraclide (pw)
(Amaranthus retr*flexus)
, Curly Dock CCD) (Sho Samuri 1tsu), and Yellow Nut Setsuzo (Y NG) (Person ■ Parking @
5aul*ntus).

Depending on the size of the plants, 20 to 4 liters per row after germination.
Many seeds were sown so that 0 seedlings grew.

Using an analytical weigher, 600 μm of the test compound was weighed onto glassine paper, placed in a 60-mm wide-mouth bottle, and dissolved in acetone or other solvent.

The 18-liter of this solution was further transferred to a new 60-mouth wide-mouth bottle, and 0.5 units (v
/v) Dilute with 22 g of the containing solution. Add this solution to 8
The seeded test flats were sprayed on a linear spray table adapted to apply an amount of 0 gallons/nacre C7481/ha). The application rate is 4 lb/neeker (4.48 slag/ha).

After treatment, test flats were heated to 70-80”F (21,1-2
The plants were placed in a greenhouse maintained at 6.6°C) and watered with sprinklers. Two weeks after treatment, the damage or control status of the plants was evaluated.
Determined against untreated control plants of the same generation. Damage rates were recorded from 10 to 100 cm for each species of plant. 0 indicates that there is no harm at all, and 100% indicates that it is completely suppressed.

The test results are shown in the following table ■.

Table ■ Pre-emergence herbicidal activity application rate - 4,48 cod/ha1 100 90 20 40 65 50 35 8
02 8090 030 80 90 20 9030
004040400 0 4 100100 50 35 100 100 90
955 100 95 65 35 90 85 5
0 956 50 25 0 25 100 100
35 807 80 90 10 60 100 10
0 100 808 95 95 45 40 100
80 95 9159 95100 55 30 1
00 90 100 9510 100100 60
20 85 100 100 9511 85 100
30 40 100 100 100 9512 8
5 85 90 75 80 95 90 9013
85 75 10 10 85 65 95 9014
40 10 80 0 65 40 65 1001
5 40 60 20 30 100 30 75 9
516 80 80 20 55 75 90 40
9517 20 - 10 25 100 95 85
9018 65 - 30 70 100 100
85 9019 4560 030 40 020 6
020 30 85 20 40 95 85 40
4521 80100 0 80 100 100 9
5 9522 20 10 0 20 75 30 4
5 1023 45 95 10 0 100 851
00 9524 -100 0 25 70 90 -
10025 - 100 25 80 100 10
0 - 10026 4015 0 0 0 10 0
3027 40 80 10 20 60 50 30
7528 65 75 0 65 100 95 7
5 5529 100 95 55 10 80 75
85 9530 20 20 20 10 40 4
0 50 2031 75 95 20 20100
95 75 1032 90 85 20 0100
85 75 3033 80 70 0 40 20
40 90 8034 60 40 0 20 951
00 100 6035 010 0 01020 2
01036 0 0 0 20100100 100
037 40 0 0 20100 60 90 -3
8 10 40 0 20 90 80 20 203
9 8010 0 0 0 0 0904060000
00 090 41 100100 85 40 95100 100
10042 60100 25 0 0 0 0 25
43 100100 45 40 80 90 901
0044 90100 0 60100100 1oo
9545 100 100 0 60 100 10
0 100 10046 20 60 0100100
100 100 2047 60 70 201001
00100 100 6048 60 0 0 0 0
0 0 4049 100100 50 10 60
20 9010050 100100 80 10
60 60 9010051 100100 9010
0100100 8510052 100100 60
10100100 6010053 020 0 0
2020 01054 104510 0 0 0 0
4055 90100 60100100100 90
10056 100100 80 10 60 60
9010057 100 100 901001001
00 8510058 90 95 0 20 20
40 4010059 95100 85 75100
100 90 9860 95100 50 5010
0100 90 9861 100100 75100
100100 95 9562 100100 95
75100100 100 8063 100100
40 65100100 100 9564 1001
00 98100100100 100 9065 1
00 100 80100100 100 100 9
0 table ■ (continued) 66 100100 75100100100 100
θ873 10010060 80100100 7
59074 100100 70 80100100
8010075 70100 0 50100100
1008076 40 90 25 10100100
100 1077 '100100 9010010
0100 85 -78 100100 801001
00100 90 ----No germination for some reason.

Blank areas indicate weeds were not tested.

Post-emergence herbicidal test This test was conducted similarly to the pre-emergence test, except that 8 different weed species were planted 10-12 days before treatment. Additionally, watering on the treated test flats was limited to the soil surface only;
I tried not to go to the leaves of germinating plants.

The results of the post-emergence herbicidal test are shown in Table ■.

Table ■ Post-emergence herbicidal activity application rate - 4,48#/ha1 60 70 20 40 60 60 35 60
2 30 70 0 50 90 85 30 803
030 0701009055 704 95 98
20 98 100 100 30 955 80
80 75 50 60 80 0 956 40 4
0 10 60 100 100 75 657 60
75 40 60 100 75 100 758
85 80 75 70 95 80 90 909
85 80 75 70 95 80 90 9010
95 85 90 60 95 95 80 951
1 50 80 35 55 100 100 95
8012 45 75 50 55 75 60 50
8013 30 60 20 60 80 50 6
0 7014 20 10 20 50 45 40
40 015 65 95 0 65 95 3010
0 8016 65 80 20 85 85 30
30 80 table ■ (continued) 17 75 80 30 70100100 85 9
018 100 95 10100100100100
9019 60 80 40 70100 75 8
0 9020 65 80 10 85 95 91)
100 7021 30 55 0 80100 80
65 8022 0 30 0 20 45 0 3
0 2023 85 90 40 85100 951
00 9024 0 80 0 70 f30 74
- 10025 100100 75 9010010
0 - 10026 45 30 0 40 70 6
5 0 4527 75 80 30 65 50 4
5 85 8528 75 60 60 75100
70 80 2529 85 85 85 75 85
65 65 8530 75 50 20 10 0
0 20 4031 60 60 20 40 40
70 100 4032 60 25 20 40
90 65 20 4033 10 0 0 10 1
0 10 100 4034 1010 0 5503
0 80 035 0 0 0106030 40 0
36 0 0 0 20 20 20 0 037 0
0 0304020 80 0BB 16) 10
10 20 10 20 20 1039 40402
0 0 0 0 58040 90 70 40 20
60 80 20 6541 60 85 85 2
0 40 60 10010042 60 50 40
70 20 40 60 6043 100 80
30 60100100 8010044 80 85
0 60 90 80 100 8045 90 9
0 10100100100 100 9046 80
100 0 60 100 100 100 100
47 100 100 0 60 100 100 1
00 10048 40 40 20 10 10 1
0 90 4049 40 40 40 80 100
100 60 6050 80 60 60 50
50 60 80 7051 80 80 95100
100100 100 9052 60 60 20
20 40 40 90 6053 102020 0
0 0 020+54 204020 5 0 0
04055 40 40 40 60 60 60 8
0 9056 80 60 60 50 50 60
80 7057 80 80 80 95100100
100 9058 60 70 10 70 10
10 20 8059 100100 90100 −
-:100 100 5060 1001001001
00 - 100 100 7061 90 85 9
0 85 - 100 100 8062 100 8
5100 75100100 100 3563 70
80 20 100 100 100 35! , 40
64 75 75 90 70 90 70 40 4
065 100 70100 55 90 95 10
0 4066 100 75100 90 95 95
100 2073 100 100 95 100
100 100 55 3074 100 95 75
100 100 100 85 4075 1001
00 30 95 80100 80 4076 80
80 75 75 100 95 95 2577
80 80 80 90 90 80 90 8078
80 85 75 85 80 95 100 50
Pre-emergence, multi-species weed control test Several compounds were tested on more types of weeds.
Pre-emergence activity tests were conducted at an application rate of 2 lb/neeker (2.24~/ha).

Weigh out 300 ~ test compounds and apply at an application rate of 40 gallons/
The test was carried out in the same manner as the pre-emergence test described above, except that the seedlings were grown under the conditions of 51.413/40.47 are.

Redroot Bigwood (pw) and Curly Dock (CD) were not used in this test and the following types of weeds were added:

Hempsesbania 5ssbanla *xaltat
a (SEAR)h@mp mesbanim The test results are shown in Table ■.

The compounds of the present invention are useful as herbicides, especially as pre-emergence herbicides, and can be used at various concentrations and at various concentrations. It can be used in the following ways. In practice, the compounds described herein are formulated as herbicidal compositions in which herbicidally effective amounts are mixed with additives and carriers as dispersants commonly used in agriculture, and the activity of the compounds is controlled in the desired manner of use. I'm trying to bring it out.

The herbicidally active compound may be present as a granulate of relatively large particles, as a wettable powder, as an emulsifiable concentrate, as a powder, as a solution, or as a formulation in some other known form. It is blended according to the desired usage mode. Preferred formulations are wettable powders, emulsifiable concentrates and granules. These formulations may contain from 0.5 inches to 95 inches or more of active ingredient by weight. The effective herbicidal amount varies depending on the nature of the seed and plant, and the application rate is approximately 0.05 to 25 lb/nika (O10227 to
11.35 kf740.47 are), preferably about 0
．． 1-10 pounds/knee car (0,0454-4.54
40.47 are).

Wettable powders are those in the form of finely divided powders that are easily dispersed in water or other dispersion media. Wettable powders are ultimately applied to the soil in dry powder form or as a dispersion in water or other liquids. Typical carriers for wettable powders include fuller's earth, kaolin clay, silica, and other readily wettable organic or inorganic diluents. Wettable powders usually contain from 5 to 95 active ingredients and usually also contain small amounts of wetting agents, dispersing agents, and emulsifying agents.

Emulsifiable concentrates can be dispersed in water or other dispersion medium in a homogeneous liquid composition and include the active ingredient and a liquid or solid emulsifier or liquid carrier such as xylene, heavy aromatic compounds,
Contains In7olone and other non-volatile organic solvents. In herbicide applications, these concentrates are dispersed in water or other liquid carrier and usually applied as a through to the treated area. The proportion of active ingredient will vary depending on the method of applying the composition, but will generally range from about 0.05 to 95.0%.

Granular formulations in which the active ingredient is supported by relatively coarse particles are
Usually applied without dilution.

Typical carriers for granular formulations include sand, 7 Jeller's earth,
Active ingredients are adsorbed or deposited with bentonite clay, vermiculite, perlite and other organic or inorganic materials.

Particulate formulations usually contain about 5 to 25 active ingredients;
It may also contain heavy aromatic naphtha, kerosene and other petroleum fractions, vegetable oil, and adhesives.

Typical wetting agents, dispersing agents and emulsifying agents used in agricultural formulations include, for example, alkyl and alkylaryl sulfonates and sulfates and their sodium salts:
Polyhydric alcohol; other surfactants. If a surfactant is used, the herbicidal formulation should be added from 0.1 to
It is about 15 inches.

Powdered formulations may also be useful for application into the soil.
It is a free-flowing mixture of the active ingredient and its dispersion medium, fine powders of talc, clay, flour or other organic or inorganic solids which serve as carriers.

Paste formulations are used for special purposes;
It consists of finely powdered active ingredients suspended uniformly in a liquid carrier such as water or oil. The formulations usually contain from about 5 to 95 parts by weight of active ingredient and may also contain minor amounts of wetting agents, dispersing agents, and emulsifying agents. In use, the paste is usually diluted and applied by spray.

Other useful formulations include completely dissolved solutions in acetone, alkylnaphthalenes, xylene, and other organic solvents at the desired concentration. A pressurized sprayer may also be used that uses a low boiling point solvent such as Freon and finely disperses the active substance through its vaporization.

The herbicidal formulations of the invention can be applied to plants in the usual manner. Powder and liquid formulations can be applied to plants using powder spreaders or boom sprayers.

The formulation is also effective in very small quantities and can be applied from airplanes in powder or spray form. Woma is a typical example.
To inhibit seed germination and seedling production, the powder or liquid formulation is applied to the soil in the conventional manner and dispersed to a depth of at least 1/2 inch below the surface. These formulations are
There is no need to mix it with soil particles as it can simply be sprayed and distributed onto the soil surface. The herbicidal formulation may be applied by adding it to the irrigation water supplied to the treated field. According to this method, as water is absorbed into the soil, the formulation also percolates. Powder, particulate or liquid formulations applied to the soil surface are dispersed below the soil surface by conventional methods such as plowing.

The herbicidal formulations of the invention may also contain other formulations. For example, fertilizers, other herbicides, fungicides, etc. Phytotoxic compounds useful in combination with the foregoing compounds include, for example, 2-he/so-f-azole-2-a+cyN-methylacetanilide, 2-chloro0-2'
, 6'-cymethyl-N-(n-norobylethyl)acetanilide, 2-chloro-2/, 6/-cyethyl-
Anilides such as N-(butoxymethyl)acetanilide; 2.4-dichlorophenoxyacetic acid, 2.4.5-)
Lichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid and its salts, esters, ides; 2,4-
♂su(3-methoxyglopylanno)-6-methylthio-1-drianone, 2-chloro-4-ethylamino-6
Triazone derivatives such as triacin, 2-nitylaminol, 4-isopropylaminol, 6-methyl-mercapto-triazine, and 3-(8
, 5-dichlorotetraphenyl)-1,1-zomethylnylia and 3-(p-10 lophenyl)-1,1-2 methylylia; Acid derivative; 5-(1,l-dimethylbenzyl)-pipe lj ten-1-car is thioate, 3-(4-chlorophenyl)-methyldiethyl car-
thioate, ethyl-1-hexahydro-1,4-7zevin-1-carpothioate, S-ethyl-hexahydro-IH-7zepin-1-carpothioate, S-propyl N, N-dibu pylthiocarbamate, S -Ethylhexahydro-IH-thiocarbamates such as azepine-1-carpothioate; 4-(methylsulfonyl)-
2,6-Sodi)CI-N, N-ft-substituted aniline, 4-trifluoromethyl-2,6-sinitro N, N-J-n
-Glopylaniline, 4-trifluoromethyl-2,6
-Anilines such as dinitro-N-ethyl-N-butylaniline, 2-(4-(2゜4-?)Irolophenoxy)
Phenoxy] Noropa IF! , 2-[1-(ethoxyiono)-butyl]-5-[2-(ethylthio)globil]
-3-Hydroxy-2-cyclohexene l-one, C±
)-butyl-2-(4-[(5-)lifluoromethyl)
-2-pyridinyloxy]phenoxy]proninoic acid n
Conductor, 5-C2-chloroo-4-(trifluoromethyl)
Sodium phenoxif-2-nitrobenzoate, 3-isonorovir-IH-2,1,3-benzothiazoazine-4 (
3H)-one-2,2-dioxide, 4-amino-6
-tert-butyl-3-(methylthio)-1-triazin-5(4M)-one, (4-7mino=6-(1,1-trimethylethyl)-3-(methylthio)-1,2,4 −)
lyascin-5(4H)-one), 8-(0,0-2 inglovir)-benzenesulfonamide, and the like.

Fertilizers useful in combination include, for example, ammonium nitrate, urea and soot phosphate. Compost, humus, sand, and others from plant organisms are also useful additives.

Representative patent attorney Hideaki Kuwahara (44) Continued priority claim from page 1 ■1984 ￥: March 7 [phase] United States (U.S.
S) [Phase] 58730198Yu July 31st [Phase] United States (
US) [Phase] 63440 Inventor Girly Uniin United States 1Crats Ping Dry 259-1 California 95129 San Jose, BU 14
23

Claims (1)

[Claims] Here, R and R1 are hydrogen, C1-4 alkyl, R''
oc(o)-1 where R is Calkyl; 1-4 R8 is chlorine, bromine, iodine or Cal-4 alkoxy; R", R4 and R are independently hydrogen or an aliphatic group, and their salts, except those of the structure, in particular, R, R' are hydrogen or C1-4 alkyl; R3
is chlorine, bromine, iodine; Ra is hydrogen, iodine, chlorine; R4 is hydrogen, halodane, C1-4 alkyl, C alkoxy, nitro, tri-1-4 fluoromethyl, 2. In the compound of claim 1 , R and R1 are hydrogen or C alkyl: 1-4 R1 is chlorine, bromine, iodine or C alkoxy: R1, R4 and RI are independently hydrogen, norodane, C alkyl, C alkoxy, 1-4 1 ~4 0CFs % Cyano, nitro, C haloalkyl 1-4 b b , R8O where R is C alkyl: n 1-4 C haloalkyl, phenyl, benzyl, 1-4 -NRR where Rd and R@ are independently Hydrogen and C alkyl; n is 0.1 or 2; RcC(0)1-4 NH-, Coconi Rc alkyl; RfC(0)-11
~4 where R is hydrogen, C alkyl, 01-41-4 haloargyl, C alkoxy; mata is 1-4 -NRgRh, where ug and Rh are independently hydrogen or C alkyl and salts thereof. 1-4 3. In the compound of claim 1, R and R1 are hydrogen or methyl; R8 is chlorine or methoxy;
Ra is hydrogen, chlorine, dimethylamino or methoxy; R
4 is hydrogen, chlorine, nitro, 5OICHI X5OIN (
CHs)s or CF; and 11 is hydrogen and salts thereof. 46 In the compound of claim 3, R11
is substituted at the 3-position, R4 is substituted at the 4-position, and RI is substituted at the 5- or 6-position, and salts thereof. 5. In the compound according to claim 3, R and R1 are hydrogen; RII & chlorine or methoxy; Ha is hydrogen, 3-chlorine, 4-methoxy, or 3-dimethylamino; and R4 is 4-chlorine, 4 -CHISO,- or 4
CFiSOm; and R1 is hydrogen and salts thereof. 6. In the compound according to claim 2, R8 is chlorine and salts thereof. 7. In the compound of Claim 1, R(3) is methyl, R1 is methyl, R1 is chlorine, Hl is hydrogen, R
4 is hydrogen, RI is 6-chlorine and its salts. 8. In the compound of claim 1, R is hydrogen, R1 is hydrogen, R1 is chlorine, R1 is hydrogen, R4 is hydrogen,
RI is 6-chlorine and its salts. 9. In the compound of claim 1, R is hydrogen, R1 is hydrogen, R1 is chlorine, R1 is hydrogen, R4 is 4-chlorine, and HI is hydrogen and its salts10. In the compound of claim 1, , R is hydrogen, R1 is hydrogen, R8 is chlorine, R1 is 3-chlorine, R4 is hydrogen and R1 is 6-chlorine and its salts 11, in the compound according to claim 1, R is hydrogen, R1 is hydrogen , Rm is chlorine, R1 is hydrogen, R4 is hydrogen, 11 is 5-trifluoromethyl and its salt 12, in the compound of claim 1, (4) R is hydrogen, R1 is hydrogen, R ratio is chlorine, Rs is 3-chlorine
R4 is 4-chlorine, R1 is hydrogen and its salt 13, in the compound of claim 1, Rt is hydrogen, R1 is hydrogen, Bg is chlorine, R1 is 3-chlorine, R4
is 4-methoxy, R1 is hydrogen and its salt 14, and in the compound of claim 1, R1 is hydrogen, R1 is chlorine, R8 is hydrogen, and 14 is 4.
-bromine R1 is hydrogen and its salt 15, in the compound of claim 1, R is hydrogen, R1 is hydrogen, R is methoxy, R1 is 3-methoxy, R4 is hydrogen, RI is hydrogen and its salt 16. In the compound according to claim 1, R is innorovir, R1 is hydrogen, R2 is chlorine, and R1 is hydrogen.
4 is 4-chlorine, R is hydrogen and its salts 17, In the compound of claim 1, R is innorovir, R1 is hydrogen, R1 is chlorine, R" 4X 3
-CHm, R' Ltt 4-CH5-802, Rl
kj. Hydrogen and Salts thereof 18, In the compound of claim 1, R is hydrogen, R1 is hydrogen, R1 is chlorine, Rs is hydrogen, and R4 is 4-
CH, 50, A method of weed control comprising applying an effective amount, wherein R and R1 are hydrogen, C alkyl, 1-4 R'0C(0)-, where R1 is C alkyl; 1-4 R''&L chlorine, bromine , iodine, or 01~.Alkoxy; RI, R4 and R11 are independently hydrogen or an aliphatic group: and salts thereof, excluding the following structures, also include R,
R1 is hydrogen or C alkyl: 1-4 R is chlorine, bromine, iodine: Ba is hydrogen, iodine or chlorine; R4 is hydrogen, halodane, C alkyl, C alkoxy, nitromata is 1-4 Fluoromethyl 2, in the method of claim 20, R and R1 are hydrogen or C alkyl; 1-4 R1 is chlorine, bromine, iodine or C alkoxy; RI XR4 and R'&X independently Hydrogen, halodane, C alkyl, ClN4 alkoxy, 1-4 (7) OCF, $cyano, nitro, Cl-4 haloalkyl,
where R and R are independently hydrogen, C0-4 alkyl; n
is 01 or 2; R(lCCO)NH-, where R
01-4 alkyl; RC(0)-% where RR is independently hydrogen or C alkyl and 1-4 their salts 2, in the method of claim 20, R and R1 are hydrogen or methyl; R1 is chlorine or methoxy;
Rs is hydrogen, chlorine or methoxy: R4 is hydrogen, chlorine,
Nitro, SO, CH field, sosN(CHm)s or C
F, ; R' is hydrogen and their salts 2, and in the method of claim 22, Ba is 3
R4 is substituted at the 4-position, RS is substituted at the 5- or 6-position, and salts thereof (8) U, in the method of claim 22, R and R1 are hydrogen HRM is chlorine or methoxy; Rs is hydrogen;
3-chlorine, 3-methoxy or 3-dimethylamino; R
4 is 4-chlorine, 4-CH2SO314CFsSOI i
R' is hydrogen and salts thereof 2, in the method of claim 24, R2 is chlorine and salts thereof 2, in the method of claim 20, R is methyl, R1 is methyl, RM is Chlorine R8 is hydrogen, R4 is hydrogen, HI is 6-chlorine and its salt 2, in the method of claim 20, R is hydrogen, R1 is hydrogen, R1 is chlorine, Rs is hydrogen, R4 is hydrogen,
RI is 6-chlorine and its salt 2, in the method of claim 20, R is hydrogen, R1 is hydrogen, 12 is chlorine, R1 is hydrogen, R4 is 4-chlorine and RS is hydrogen and its salt 2, patent In the method of claim 20, R is hydrogen, R1 is hydrogen, BN is chlorine, R1 is 3-chlorine, R4 is hydrogen, and R1 is 6-chlorine and its salts 30. , R is hydrogen, R1 is hydrogen, R1 is chlorine, R3 is hydrogen, R4 is hydrogen, R1 is 5-trifluoromethyl and its salts 31, in the method of claim 20, R is hydrogen, R1 is hydrogen, R1 is chlorine, Ba is 3-chlorine, R4 is 4-chlorine, RI is hydrogen and its salts 32, in the method of claim 20, R is hydrogen, R1 is hydrogen, R1 is chlorine, Ba is 3-chlorine, R4 is 4-methoxy, RI is hydrogen and its salts 33, in the method of claim 20, R is hydrogen, R1 is hydrogen, R1 is chlorine, R1 is hydrogen, R4 is 4-
Bromine, R1 is hydrogen and its salts 34, in the method of claim 20, R is hydrogen, R1 is hydrogen, B2 is methoxy, R3 is 3-methoxy, B4 is hydrogen, R5 is hydrogen and its salts 35, In the method of Range 20, R is isopropyl, R1 is hydrogen, R1 is chlorine, R3 is hydrogen, R
4 is 4-chlorine, R1 is hydrogen and its salt 36, in the method of claim 20, R is hydrogen, R1 is hydrogen, RN is chlorine, R1 is 3-CH,O, R
' is 4- CH, So,
CH5SO, 1B is hydrogen and its salt 38, in the method of claim 31, sodium isopropylamine, triethylamine, potassium salt