CN101838227A - Safener of benzamide herbicide - Google Patents

Abstract

The invention provides a safener of a benzamide herbicide and use thereof combined with the herbicide, and the safener has a structural general expression I, wherein R1, R2, R3, R4 and R5 are defined as a specification.

Description

Safener of benzamide herbicide

The invention relates to a safener of benzamide herbicide.

Background art the german bayer company disclosed in 2004 a process for the preparation of acylsulfamoylbenzamides (US7608736) of formula i,

on the basis of the patent, the invention carries out structural modification on the compound and synthesizes a completely different compound.

The invention relates to benzamide compounds and various isomers thereof, and salts applicable to agriculture, and the compounds have a structural general formula I:

wherein,

x is CH or N;

R₁is H, - (CH)₂)_p，-heterocyclyl or hydrocarbyl, wherein the last 2 of said groups are unsubstituted or substituted with one or more groups selected from: element, C₁-C₆Alkyl radical, C₁-C₆ alkyl, C₁-C₆Alkoxy, cyano and nitro;

R₂is H, C₁-C₆Alkyl radical, C₂-C₆Alkenyl radical, C₂-C₆Alkynyl, C₁-C₆Alkoxy radical, C₂-C₆Alkenyloxy, wherein the last 5 of said groups are unsubstituted or substituted with one or more groups selected from the group consisting of: element, C₁-C₄Alkoxy and C₁-C₄Alkylthio radical, C₁-C₄Dialkylamino radical, C₁-C₄An alkyl amino group or a substituted or unsubstituted alkyl group,

R₁and R₂Together with the nitrogen atom to which they are attached form a 3-9 membered saturated or unsaturated ring;

R₃and R₅Each independently is element, C₁-C₆Alkyl radical, C₁-C₆ alkyl, C₁-C₆Alkoxy, S (O)_q-C₁-C₆Alkyl radical, C₁-C₆Alkoxycarbonyl, -CO-aryl, cyano and nitro; or two adjacent R₅Radical formto-OCH₂-CH₂-a moiety;

R₄is H, C₁-C₄Alkyl radical, C₂-C₄Alkenyl, or C₂-C₄An alkynyl group;

n is 0 to 4;

m is 0 to 5;

p is 0 or 1;

q is 0, 1 or 2;

especially as herbicidal compositions of interest, comprising one or more safeners of the present compounds of formula I, I-a, I-b, I-c, I-d, I-e, I-f:

also of particular interest are various herbicidal compositions including, among others, flucarbazone, foramsulfuron, iodosulfuron, sulfenamide, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, thifensulfuron-methyl, tribenuron-methyl, cloransulam-methyl, chlorimuron-ethyl, ethoxysulfuron, flazasulfuron-methyl, florasulam, flumetsulam, halosulfuron-methyl, imazapyr, imazamox, imazethapyr, mesosulfuron, prosulfuron, sulfosulfuron, amidosulfuron, chlorsulfuron, imazosulfuron, triasulfuron, metsulfuron, cyclosulfamuron, primisulfuron, azimson, bensulfuron, bispyribac, rimsulfuron, triflusulfuron, sulcotrione, isoflurtamone, mesotrione, Topramezone, metribuzin, bentazone, bromopiclonitrile, terbuthylazine, and benthiazine, furoprione, clethodim, diclofop-methyl, clethodim, clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fluazifop-p-ethyl, haloxyfop-R-methyl, haloxyfop-ethyl-ethoxy-ethyl, propaquizafop-ethyl, quizalofop-p-ethyl, acetochlor, s-metolachlor, flumioxazin, flumetsulam, sulfentrazone, dicamba, 2-methyl-4-chloro, 2-methyl-4-chloroacetic acid, 2, 4-D, clopyralid, fluroxypyr, clopyralid, clomedine, glufosinate, and pendimethalin, wherein the weight ratio of the present compound I to the above herbicides is 1: 200-200-1.

Compound preparation embodiments: the invention is further illustrated by the following examples, which are not intended to be limiting. All parts and percentages in the examples are by weight.

Examples preparation of a typical Compound I-c:

to a mixture of 10.3g of Compound 1(50mmol) and 9.83g of Compound 2(52.5mmol) in 135ml of dichloromethane was added 12.11g (130mmol) of picoline at room temperature, followed by stirring and cooling to-5 deg.C, then dropwise addition of a solution of methanesulfonyl chloride 6.89g (60mmol) in 10ml of dichloromethane at that temperature, completion of dropwise addition for 30 minutes, heating to room temperature and stirring for reaction for 3 hours, then dropwise addition of 10ml of water, cooling of the mixture to 0 deg.C, filtration, and washing with heptane to obtain the desired product. Purity 98%, yield 95%, melting point 218-.

Claims (9)

1. Benzamide compounds and various isomers thereof, and salts suitable for agriculture, having the structural formula I:

wherein,

x is CH or N;

R₁is H, - (CH)₂)_p-heterocyclyl or hydrocarbyl, wherein the last 2 of said groups are unsubstituted or substituted with one or more groups selected from: element, C₁-C₆Alkyl radical, C₁-C₆ alkyl, C₁-C₆Alkoxy, cyano and nitro;

R₂is H, C₁-C₆Alkyl radical, C₂-C₆Alkenyl radical, C₂-C₆Alkynyl, C₁-C₆Alkoxy radical, C₂-C₆Alkenyloxy, wherein the last 5 of said groups are unsubstituted or substituted with one or more groups selected from the group consisting of: element, C₁-C₄Alkoxy and C₁-C₄Alkylthio radical, C₁-C₄Dialkylamino radical, C₁-C₄An alkyl amino group, or,

R₁and R₂Together with the nitrogen atom to which they are attached form a 3-9 membered saturated or unsaturated ring;

R₃and R₅Each independently is element, C₁-C₆Alkyl radical, C₁-C₆ alkyl, C₁-C₆Alkoxy, S (O)_q-C₁-C₆Alkyl radical, C₁-C₆Alkoxycarbonyl, -CO-aryl, cyano and nitro; or two adjacent R₅Radical formation of-OCH₂-CH₂-a moiety;

R₄is H, C₁-C₄Alkyl radical, C₂-C₄Alkenyl, or C₂-C₄An alkynyl group;

n is 0 to 4;

m is 0 to 5;

p is 0 or 1;

q is 0, 1 or 2.

2. The present invention as claimed in claim 1, wherein the compounds are included as safeners for one or more antidotal agents, which compounds can be used in combination with one or more herbicides, including flucarbazone, foramsulfuron, iodosulfuron, metosulam, metsulfuron, nicosulfuron, primisulfuron, prosulfuron, thifensulfuron, tribenuron, cloransulam, chlorimuron, ethoxysulfuron, flazasulfuron, florasulam, flumetsulam, halosulfuron, imazapyr, imazapic, imazamox, imazethapyr, methasulfuron, metsulfuron, prosulfuron, sulfosulfuron, imazasulfuron, imazaquin, triasulfuron, sulfometsulfuron, sulfometuron, sulfometsulfuron, pyrazosulfuron, sulfometsulfuron, bensulfuron, bispyrisulfuron, sulfosulfuron, triflusulfuron, sulcotrione, clomazone, mesotrione, Topramezone, metribuzin, bentazone, bromoxynil, terbuthylazine, dichlorfon, flurtamone, clethodim, sethoxydim, clethodim, clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-p-ethyl, fluazifop-p-ethyl, haloxyfop-R-methyl, haloxyfop-ethyl, propaquizafop-p-ethyl, quizalofop-p-ethyl, acetochlor, metolachlor, flumioxazin, fomesafen, sulfluramid, sulfentrazone, dicamba, 2 m 4 chloro, 2 m 4 chloroacetic acid, 2, 4D, clopyralid, fluroxypyr, dichlorvonicamid, pralidine, and pendimethalin in a weight ratio of the compound of claim 1 to the above herbicide of 1: 200-1.

3. A combination of herbicides according to claim 2 wherein the benzamide compound is:

R₁is H, or ethyl;

R₂is ethyl, cyclopropyl or isopropyl;

R₃and R₄Is H;

R₅is H, Cl, methyl or methoxy.

4. A combination of herbicides according to claims 1-3 wherein the benzamides are:

5. a combination of herbicides according to claims 1-4 characterised in that as the present case the benzamide compounds are used for plant dressing and with pre-and post-emergence for said herbicides; the plant seeds are additionally dressed with one or more fungicides and/or with insecticides.

6. A combination of herbicides as claimed in claims 1 to 5 for use in the control of harmful plants in monocotyledonous plant crops.

7. A combination of herbicides as claimed in claim 6 for use in maize, wheat, rye, barley, oats, rice, sorghum, cotton and soybean.

8. The combination of herbicides according to claim 7, wherein the plant is genetically modified or obtained by mutational selection.

9. The combination of herbicides according to claims 1 to 8, which is formulated as an emulsion, an oil suspension, a solution (including emulsifiable concentrate), a wettable powder, a dust, a granule, and a concentrated composition.