CN1327984A - Substituted triazole, imidazole or pyrazole herbicides - Google Patents
Substituted triazole, imidazole or pyrazole herbicides Download PDFInfo
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- CN1327984A CN1327984A CN 00110501 CN00110501A CN1327984A CN 1327984 A CN1327984 A CN 1327984A CN 00110501 CN00110501 CN 00110501 CN 00110501 A CN00110501 A CN 00110501A CN 1327984 A CN1327984 A CN 1327984A
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Abstract
The present invention relates to the substituted or unsubstituted triazole, imidazole, or pyrazole compounds whose benzene ring has the heterocycle substituted radical, their composition, and the application of said compounds in herbiciding. The herbicides containing them can be used in wheat, corn and soybean field.
Description
The invention belongs to the agricultural herbicide field.What relate to is a class novel heterocyclic compounds and with method of these compound managements of weeds and the use that contains the weedicide of these compounds.
Weeds especially for satisfying agricultural-food such as necessary grain of human primary demand and fiber, are caused very big infringement as cotton, paddy rice, corn, wheat, soybean etc. to crop.The infringement of avoiding when killing or suppressing weed growth or reducing crop is a kind of effective way of improving agriculture production.Although existing many weedicides, but still need more effective, safer weedicide.
The compound general formula following (i) that EUROPEAN PATENT OFFICE announces in EP0083055A2 on July nineteen eighty-three 6
Wherein:
R
1Be H, alkyl, low cycloalkyl, low cycloalkyl, low alkyl (low) cycloalkyl, low cycloalkyl (low) alkyl, low thiazolinyl, low cycloalkenyl group, low cycloalkenyl group (low) alkyl, phenyl, cyano group (low) alkyl, low alkynyl, low alkyl imino, low alkylthio (low) alkyl, benzyl, halo (low) alkyl or low cycloalkyl imino-;
R
2Be H, low alkyl, low-alkoxy;
The X chlorine or bromine;
Y is oxygen or imido;
Z is oxygen or sulphur.
The compound general formula that EUROPEAN PATENT OFFICE announced among the EP0273417Al on June 6th, 1988 is (ii) following: wherein:
X and Y are H or halogen;
Z is-SCH (R) COOR
1
R is H, alkyl; R
1Be alkyl, cycloalkyl, or epoxy alkyl, perhaps Q is an alkyl in COOQ, or Y all links to each other with phenyl ring with Z,
Wherein, R
2Be H or alkyl; R
3Be alkyl: alkenyl or alkynyl.
More than all reported compound in two pieces of patents with weeding activity.Yet, do not see the report of substituted triazole of the present invention, imidazoles, pyrazole compound weedicide.
In order to satisfy the requirement on the agricultural, the invention provides the using method of a kind of new new herbicidal compound of substituted triazole, imidazoles, pyrazolesization and management of weeds thereof and contain the application of weedicide on agricultural of these compounds.As broad-spectrum herbicide, can effectively control the weeds in soybean, corn and the wheat paddock, and these crops are had security.
These new compounds can be expressed by following general formula I:
Wherein:
R
1Be selected from H, F, Br, Cl, NO
2Or CN;
R
2Be selected from F, Cl, Br, H or CN;
R
3Be selected from H, CN, halogen, alkyl, thiazolinyl, alkynyl, cycloalkyl, cycloalkenyl group, cycloalkenyl group, haloalkyl, haloalkenyl group, halo alkynyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, alkoxyl group, alkylthio, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, the alkyl sulfenyl cycloalkyl, cyano alkoxy, cyano group alkyl, cyano group cycloalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, all these groups can further be replaced;
R
4, R
5Be selected from H respectively, halogen, CN, alkyl, cycloalkyl, haloalkyl, alkoxyl group; alkylthio, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, cyano alkoxy; the cyano group alkyl, cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, CO
2R
6, CONR
6R
13, OR
6, SR
6, SO
2R
6, NR
6R
13, SO
2NR
6R
13, cyano alkoxy, the cyano group alkyl, the cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, aryl, aralkyl or heteroaralkyl, all these groups can further be replaced;
R
6Be selected from H, alkyl, cycloalkyl, alkoxyl group, alkylthio, alkyl sulfonyl alkyl, the alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, cyano alkoxy, cyano group alkyl, cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, aryl or aralkyl, all these groups can further be replaced;
R
7Be selected from H, alkyl, thiazolinyl, alkynyl, cycloalkyl, alkyl sulfonyl alkyl; the alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl cyano alkoxy, cyano group alkyl, cyano group cycloalkyl; haloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, or COR
9, all these groups can further be replaced;
R
8Be selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl group, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, the alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, cyano alkoxy, the cyano group alkyl, cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, aryl or aralkyl, all these groups can further be replaced;
R
9Be selected from alkyl, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, the alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, thiazolinyl, alkynyl, cyano alkoxy, cyano group alkyl, the cyano group cycloalkyl, haloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl or cycloalkyl, all these groups can further be replaced;
R
10Be selected from H, halogen, NH
2, alkyl, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, alkyl sulfenyl cycloalkyl, alkyl sulfonyl cycloalkyl, haloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, cyano alkoxy, cyano group alkyl, cyano group cycloalkyl, CN, CO
2(alkyl), CONH (alkyl), CON (alkyl)
2Wherein each alkyl is identical or different, CH
2CN, CH
2CH=CH
2, CH
2CCH, CH
2CO
2(alkyl), CH
2OCH
3Or CH
2-1,2, the 4-triazole, all these groups can further be replaced:
R
11Be selected from H, CN, alkyl, haloalkyl or CO
2(alkyl);
R
12Be selected from H, alkyl, CO
2R
6, CONR
6R
13, OR
6, SR
6, SO
2R
6, SO
2NR
6R
13Or NR
6R
13:;
R
13Be selected from H, alkyl, aryl or aralkyl;
A is selected from N or CH, and B is selected from N or CR
10, have one among A, the B at least and should be N;
Z is selected from O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X can be selected from O, S, NR
12, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (halogen) CO
2, CH
2CH (halogen) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (halogen) CONH or CH
2CH (halogen) CONH;
When Z was O, X can be selected from CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (halogen) CO or CH
2CH (halogen) CO;
When Z is CO, CS, CONR
12Or CSNR
12The time, X can be selected from O, S, CO, OCH (R
6), CH=C (halogen), CH
2CH (halogen), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (halogen) CONH, CH
2CH (halogen) CONH or NR
12
Q is selected from NR
7COR
8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 or Q16 wherein:
Q1 is 4,5,6,7-tetrahydric phthalimide-2-base,
Q2 is 5,6,7,8-tetrahydrochysene-1,2, and 4-triazole [4,3-a] pyridines-3 (2H)-ketone-1-base,
Q3 is 5,6,7,8-tetrahydrochysene-1H, 3H-[1,3,4] thiadiazoles [3,5-a] pyridazine imines-1-base,
Q4 is 4,5,6,7-imidazolidine [1,5-a] pyridine-1,3 (2H, 5H)-diketone-2-base,
Q5 is 1,6,8-three nitrogen dicyclos [4,3,0]-nonane-7, and 9-diketone-8-base,
Q6 is 5-(1-methyl ethylene)-2,4-oxazoline diketone-3-base,
Q7 is 5-(1, the 1-dimethyl ethyl)-1,3,4-oxadiazole-2 (3H)-ketone-3-base,
Q8 is a 4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, and 2,4-triazole-5 (1H)-ketone-1-base,
Q9 is the 2-methyl isophthalic acid, 2, and 4-oxadiazole ketone-3,5-diketone-4-base,
Q10 is 4-chloro-1-methyl-5-difluoro-methoxy-1H-pyrazole-3-yl,
Q11 is 4-bromo-1-methyl-5-Trifluoromethyl-1 H-pyrazole-3-yl,
Q12 is 1-R
10Replacement-6-trifluoromethyl-2,4-pyrimidine dione-3-base,
Q13 is 1-R
10Replacement-6-Trifluoromethyl-1,3,5-triazine-2,4-diketone-3-base,
Q14 is 4-R
12, 5-R
11-two replace-4,5-dihydro-1,2, and 4-t triazine-3 (2H)-ketone-2-base,
Q15 is 4-R
10Replace-1,2, and 4-triazine-3,5 (2H, 4H)-diketone-2-base
Q16 is 5-methyl-6-oxygen-4-(trifluoromethyl)-6H-pyridazine-1-base;
And the salt preparation that can on agricultural, use.
" aryl " among the present invention refers to monocycle or polynuclear compound, as benzene, and naphthalene, indenes, anthracene, dicyclopentadiene and, fluorenes, acenaphthene, phenanthrene and azulene to dihydrobenzene.
" heteroaryl " refers to monocycle or polycyclic furans, thiophene, pyrroles ， isoxazole ， oxazole, different thiadiazoles, thiazole, pyrazoles, imidazoles, 1,2,3-triazoles, 1,2, the 4-triazole, tetrazolium, 1,2,3-thiadiazoles, 1,2, the 4-thiadiazoles, 1,3,4-thiadiazoles, 1,2, the 3-thiadiazoles, 1,2,4-thiadiazoles, 1,3, the 4-thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, cumarone, thionaphthene, indoles, benzoisoxazole, benzoxazole, benzisothiazole, benzothiazole, benzopyrazoles, benzoglyoxaline, benzotriazole, 1,2-methylenedioxyphenyl, ethylene dioxy base benzene, quinoline and isoquinoline 99.9.The structural formula of above-mentioned " Q " heterocyclic group of mentioning is as follows:
R wherein
10And R
11As previously mentioned." alkyl " comprises the alkyl group of side chain and straight chain.Typical alkyl has methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, iso-octyl, nonyl, decyl, undecyl, dodecyl and other.
" cycloalkyl " refers to the compound of fatty family ring structure, as cyclopropane, tetramethylene, pentamethylene, hexanaphthene, suberane, cyclooctane and other.
" haloalkane " refers to one or more halogen group substituted alkyls.
" halogen " refers to fluorine, chlorine, bromine or iodine.
" alkyl sulfonyl alkyl " refers to alkyl sulphonyl (alkyl-SO
2) substituted alkyl, as the sulfonyloxy methyl methyl.
" alkyl sulfenyl alkyl " refers to alkyl sulphinyl, and (substituted alkyl of alkyl-SO) is as methyl sulfinyl methyl.
" thiazolinyl " refers to undersaturated hydrocarbon group, contains one or two pair key on the straight or branched.
" cycloalkenyl group " refers to the aliphatics ring and contains one or two pair key, as cyclopentenes, tetrahydrobenzene, and 1,4-tetrahydrobenzene and other.
" haloalkene " refers to one or more halogen and asks for for thiazolinyl.
" alkynyl " refers to undersaturated hydrocarbon group, contains one or two triple bond in the straight or branched.
" aralkyl " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of aryl replacement.
" heteroaralkyl " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of heteroaryl replacement.
The alkyl that " alkoxyl group " refers in side chain or the straight chain is connected with Sauerstoffatom, and typical alkoxyl group has methoxyl group, oxyethyl group, positive propoxy, isopropoxy, tert.-butoxy and other.
" halogenated alkoxy " refers to one or more halogen rope atom substituted alkoxies.
The alkyl that " alkylthio " refers in side chain or the straight chain is connected with sulphur atom.
" halogenated alkylthio " refers to one or more halogen atom substituted alkane sulphur bases.
The salt preparation available acid of The compounds of this invention has hydrochloric acid, Hydrogen bromide, hydroiodic acid HI, sulfuric acid, nitric acid, phosphoric acid, oxalic acid, acetate, propionic acid, oxyacetic acid, methylsulphonic acid, toluenesulphonic acids, Phenylsulfonic acid, (C
2-C
20) alkyl benzene sulphonate (ABS), sodium pyrosulfate.
Other agricultural salt can be formed by the mixture of The compounds of this invention and metal-salt (as zinc chloride or iron(ic) chloride).
Comparatively concrete compound is the represented compound of general formula I among the present invention, wherein:
R
1Be H, F, Br, Cl, NO
2Or CN;
R
2Be F, Cl, Br, H or CN;
R
3Be H, CN, halogen, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulphinyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl basic ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyano group (C
1-C
12) alkoxyl group, cyano group (C
1-C
12) alkyl, cyano group ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkane, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, all these groups all may be undertaken 1-3 time by following radicals and replace, as bromine, and chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or nitro:
R
4And R
5Be H, halogen and CN; (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) base, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyano group (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, CO
2R
6, CONHR
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, N ((C
1-C
12) a alkyl) R
6, SO
2N ((C
1-C
12) alkyl) R
6, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, all these groups all may be undertaken 1-3 time by following radicals and replace, i.e. bromine, chlorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-oxane-2-base or nitro;
R
6Be H, (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, aryl or aryl (C
1-C
12) alkyl;
R
7Be H, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl or COR
9
R
8Be (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, ring (C
3-C
8) thiazolinyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
2) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
6) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, aryl or aryl (C
1-C
12) alkyl;
R
9Be H, (C
1-C
12) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio or halo ring (C
3-C
8) alkyl;
R
10Be H, chlorine, NH
2, (C
1-C
12) alkyl, halo (C
1-C
12) ether, CN, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, CO
2(C
1-C
12) alkyl, CONH (C
1-C
12) alkyl, CON ((C
1-C
12) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
12) alkyl, CH
2OCH
3Or CH
2-1,2, the 4-triazole;
R
11Be H, CN, (C
1-C
12) alkyl, halo (C
1-C
12) alkyl or CO
2(C
1-C
12) alkyl;
R
12Be H, (C
1-C
12) alkyl, CO
2R
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, SO
2N ((C
1-C
12) alkyl) R
13Or N ((C
1-C
12) alkyl) R
13
R
13Be H, (C
1-C
12) alkyl, aryl or virtue (C
1-C
12) alkyl;
A is N or CH, and B is N or CR
10, have one among A, the B at least and should be N;
Z is O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X is O, S, NR
12, CO
2, OCH (R
6) CO
2SCH (R
6) CO
2, CH=C (Cl) CO
2, CH
2CH (Cl) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH or CH
2CH (Cl) CONH;
When Z is O, X is CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (Cl) CO or CH
2CH (Cl) CO;
When Z is CO, CS, CONR
12Or CSNR
12, X is O, S, CO, OCH (R
6), CH=C (Cl), CH
2CH (Cl), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH, CH
2CH (Cl) CONH or NR
12
Q is NR
7COR
8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16;
And on agricultural applicable salt preparation.
Among the present invention more specifically compound be the represented compound of general formula I, wherein:
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, bromine, chlorine, fluorine, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
6) alkynyl, halo (C
1-C
6) alkyl, halo (C
2-C
6) thiazolinyl, halo (C
2-C
6) alkynyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, aryl, heteroaryl, virtue (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, wherein aryl or heteroaryl are furans, naphthalene, and phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole, aryl and heteroaryl can be undertaken 1-3 times by following radicals and replace, as bromine, chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or ammonia;
R
4And R
5Be H, bromine, chlorine, fluorine, CN, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
6) alkyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, CO
2R
6, CONHR
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, N ((C
1-C
12) alkyl) R
6, SO
2N ((C
1-C
12) alkyl) R
6, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, wherein aryl or heteroaryl are furans, naphthalene, and phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole it is reported that aryl and heteroaryl may be undertaken 1-3 times by following radicals and replace, as bromine, chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or nitro;
R
6Be H, (C
1-C
12) alkyl, aryl or aryl (C
1-C
6) alkyl, wherein aryl is naphthyl or phenyl;
R
7Be H, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl or COR
9
R
8Be (C
1-C
12) alkyl, halo (C
3-C
8) alkyl, ring (C
3-C
8) thiazolinyl, halo (C
1-C
12) alkyl, aryl or aryl (C
1-C
6) alkyl;
R
9Be H, (C
1-C
6) alkyl, (C
2-C
12) thiazolinyl, (C
2-C
6) alkynyl, ring (C
3-C
8) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
12) alkyl;
R
10Be H, chlorine, NH
2, (C
1-C
6) alkyl, halo (C
1-C
12) alkyl, CN, CO
2(C
1-C
12) alkyl, CONH (C
1-C
12) alkyl, CON ((C
1-C
12) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
12) alkyl, O or CH
2-1,2, the 4-triazole;
R
11Be H, CN, (C
1-C
6) alkyl, halo (C
1-C
12) alkyl, halo (C
1-C
6) alkyl, CO
2(C
1-C
12) alkyl;
R
12Be H, (C
1-C
8) alkyl, CO
2R
6, CON ((C
1-C
8) alkyl) R
6, OR
6, SR
6, SO
2R
6, SO
2N ((C
1-C
8) alkyl) R
13Or N ((C
1-C
8) alkyl) R
13
R
13Be H, (C
1-C
8) alkyl, aryl (C
1-C
6) alkyl, wherein aryl is naphthyl or phenyl;
A is N or CH, and B is N or CR
10, have one among A, the B at least and should be N;
Z is O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X is O, S, NH, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (Cl) CO
2, CH
2CH (Cl) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH or CH
2CH (Cl) CONH;
When Z was O, X was CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (Cl) CO or CH
2CH (Cl) CO;
When Z is CO, CS, CONR
12Or CSNR
12, X is O, S, CO, OCH (R
6), CH=C (Cl), CH
2CH (Cl), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH, CH
2CH (Cl) CONH or NR
12
Q is NR
7COR
8, or Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 or Q16;
And by hydrochloric acid, sulfuric acid, acetate, propionic acid, the formed salt preparation that can on agricultural, use of phosphoric acid or oxalic acid.
The further concrete compound of the present invention is the represented compound of general formula I, wherein:
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, bromine, chlorine, fluorine, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
6) alkynyl, halo (C
1-C
6) alkyl, halo (C
2-C
6) thiazolinyl, halo (C
2-C
6) alkynyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-two chloro-3-furyls, 1-naphthyl, 2-naphthyl, phenyl, 4-methylbenzene, 4-p-methoxy-phenyl, the 4-nitrophenyl, 4-fluorophenyl, 4-chloro-phenyl-, the 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l, 4-benzonitrile base, 3-(1,3-diox-2-yl) phenyl, the 2-fluorophenyl, the 2-chloro-phenyl-, 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3, the 5-dichlorophenyl, the 2,4 difluorobenzene base, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-fluorophenyl, 3-chloro-5-trifluoromethyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-two chloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-two chloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxyl group-4-pyridyl, 2-cyanogen-4-pyridyl, 2,6-two fluoro-4-pyridyl, 2,6-two chloro-4-pyridyl, the 2-thienyl, the 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-two chloro-3-thienyls;
R
4And R
5Be H, bromine, chlorine, fluorine, CN, (C
1-C
6) alkyl, cyanogen generation (C
5-C
6) alkyl, halo (C
1-C
6) alkyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, CO
2R
6, CONHR
6, CON ((C
1-C
6Alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-two chloro-3-furyls, 1-naphthyl, 2-naphthyl, phenyl, 4-tolyl, 4-p-methoxy-phenyl, the 4-nitrophenyl, 4-fluorophenyl, 4-chloro-phenyl-, the 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l 4-benzonitrile base, 3-(1,3-diox-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-fluoro-5-Trifluoromethoxyphen-l, 3,4, the 5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-two chloro-2-pyridyl, the 3-pyridyl, 5-bromo-3-pyridyl 1,5,6-two chloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, the 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxyl group-4-pyridyl, 2-cyanogen-4-pyridyl, 2,6-two fluoro-4-pyridyl 2,6-two chloro-4-pyridyl, the 2-thienyl, the 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-two chloro-3-three thienyls;
R
6Be H, (C
1-C
6) alkyl, 1-naphthyl, 2-naphthyl, phenyl, the 4-aminomethyl phenyl, 4-p-methoxy-phenyl, 4-nitrophenyl, 4-fluorophenyl, the 4-chloro-phenyl-, 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l, 4-cyanogen are for phenyl, and 3-(1,3-diox-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-fluoro-5-trifluoromethyl or 3,4, the 5-trifluorophenyl;
R
7Be H, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
6) alkyl or COR
9
R
8Be (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
12) alkyl, 1-naphthyl, 2-naphthyl, phenyl, the 4-aminomethyl phenyl, 4-p-methoxy-phenyl, 4-nitrophenyl, 4-fluorophenyl, the 4-chloro-phenyl-, 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, the 4-Trifluoromethoxyphen-l, the 4-fluorophenyl, 3-(1,3-diox-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-cyanogen-5-trifluoromethyl or 3,4, the 5-trifluorophenyl;
R
9Be H, (C
1-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
5-C
6) alkyl or halo (C
1-C
6) alkyl;
R
10Be H, NH
2, (C
1-C
6) alkyl, halo (C
1-C
6) alkyl, CN, CO
2(C
1-C
6) alkyl, CONH (C
1-C
6) alkyl, CON ((C
1-C
6) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
6) alkyl, CH, OCH
3Or CH
2-1,2, the 4-triazole;
R
11Be H, CN, (C
1-C
6) alkyl, halo (C
1-C
6) alkyl or CO
2(C
1-C
6) alkyl;
R
12Be H, (C
1-C
8) alkyl, CO
2(C
1-C
6) alkyl, CON ((C
1-C
6) alkyl)
2, O (C
1-C
6) alkyl, S (C
1-C
6) alkyl, SO
2(C
1-C
6) alkyl, SO
2N ((C
1-C
6) alkyl)
2Or N ((C
1-C
6) alkyl)
2
R
13Be H, (C
1-C
6) alkyl, aryl or aryl (C
1-C
4) alkyl, wherein aryl is naphthyl or phenyl;
A is N or CH, and B is N or CR
10, have one among A, the B at least and should be N;
Z is O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X is O, S, NH, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (Cl) CO
2, CH
2CH (Cl) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH or CH
2CH (Cl) CONH;
When Z was O, X was CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (Cl) CO or CH
2CH (Cl) CO;
When Z is CO, CS, CONR
12Or CSNR
12The time, X is O, S, CO, OCH (R
6), CH=C (Cl), CH
2CH (Cl), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH, CH
2CH (Cl) CONH or NR
12
Q is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 or Q16; And by hydrochloric acid, acetate, the prepared salt preparation that can on agricultural, use of phosphoric acid or oxalic acid.
The present invention can be prepared by following process by the represented compound of general formula I: reaction 1
Among above-mentioned intermediate II and the III, when X is CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH
2CH (Cl) CO
2Or CH=C (Cl) CO
2And Y is OH or NH
2The time, with chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF) ， diox, acetone or butanone are solvent, intermediate II or one of its sodium salt, sylvite and following reagent react: SOCl
2, (COCl)
2, COCl
2, PCl
3Or POCl
3, generate acyl chlorides; Acyl chlorides reacts (under alkaline condition, as Et with intermediate III again
3N, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3), control reaction temperature refluxes at-40 ℃～reaction solution, can generate the represented compound of general formula I in 3 minutes-8 hours.
Intermediate II can be by ester (made by currently known methods, chatted in EP0083055A2) and K
2CO
3, NaOH, or KOH reacts in ethanol, and then obtain with mineral acid (example hydrochloric acid) reaction.
Intermediate III (R wherein
3Be alkyl) can be by known response by aldehyde and IV at ammoniacal liquor or do not have to make under the ammoniacal liquor condition.
X in intermediate II is O, and the Y in S or NH, the intermediate III is Cl, OSO
2CH
3, when waiting, can be under alkaline condition (as triethylamine, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3, NaHCO
3, NaH, NaOCH
3, NaOC
2H
5), in following solvents: tetrahydrofuran (THF) ， diox, acetone, butanone, acetonitrile, N, dinethylformamide is refluxed at-40 ℃～reaction solution by intermediate II and intermediate III control reaction temperature, obtains the represented compound of general formula I in 30 minutes to 18 hours.Reaction 2
In the intermediate II, X is CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH
2CH (Cl) CO
2Or CH=C (Cl) CO
2:
Intermediate II or its sodium salt, sylvite and following reagent SOCl
2, (COCl)
2, COCl
2, PCl
3Or POCl
3At solvent such as methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF) ， diox, reaction produces acyl chlorides in acetone or the butanone; The acyl chlorides that is produced again with intermediate V reaction (under alkaline condition as: triethylamine, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3), control reaction temperature refluxed at-40 ℃～reaction solution, got the represented compound of general formula I from 3 minutes to 8 hours.
Intermediate V can be prepared by currently known methods, sees EP0567827Al:
Reaction 3
The salt of general formula I can by I in ethanol or other solvent with HCl, CH
3CO
2H, H
3PO
4, HO
2CCO
2H etc. or other acid-respons make.Reaction formula is as follows:
The compound of general formula I sees Table 1-25, " Ph " expression phenyl in these tables, " Ph-4-Cl " expression 4-chloro-phenyl-, " Ph-4-F " expression 4-fluorophenyl, " CH
2Ph " expression benzyl, " CH
2" " Me " represents methyl to Ph-4-Cl for expression 4-benzyl chloride base, " 3-Py " expression 3-pyridyl, and " Et " represents ethyl.
Table 1
Zai compound general formula I Zhong: A=B=N, Q=Q1 No R1 R
2 X R
3 R
4 R
5
1 F Cl CO
2 H H H
2 F Cl CO
2 CH
3 H H
3 F Cl CO
2 H CH
3 CH
3
4 F Cl CO
2 C
2H
5 Ph-4-Cl H
5 F Cl CO
2 H H SCH
3
6 F Cl CO
2 CN H H
7 F Cl CO
2 Ph-4-Cl H H
8 F Cl CO
2 CH
2Ph-4-Cl H H
9 F Cl CO
2 3-Py H H
10 F Cl OCH
2CO
2 H H H
11 F Cl OCH
2CO
2 CH
3 H H
12 F Cl OCH
2CO
2 H CH
3 CH
3
13 F Cl OCH
2CO
2 C
2H
5 Ph-4-Cl H
14 F Cl OCH
2CO
2 H H SCH
3
15 F Cl OCH
2CO
2 CN H H
16 F Cl OCH
2CO
2 Ph-4-Cl H H
17 F Cl OCH
2CO
2 CH
2Ph-4-Cl H H
18 F Cl OCH
2CO
2 3-Py H H
19 F Cl OCH(CH
3)CO
2 H H H
20 F Cl OCH(CH
3)CO
2 CH
3 H H
21 F Cl OCH(CH
3)CO
2 H CH
3 CH
3
22 F Cl OCH(CH
3)CO
2 CH
3 Ph CH
3
23 F Cl CH＝C(Cl)CO
2 H H H
24 F Cl CH
2CH(Cl)CO
2 H H H
25 F Cl OCH(CH
3)CO
2 CN H H
26 F Cl O H H H
27 F Cl O CH
3 H H
28 F Cl O H CH
3 CH
3
29 F Cl O CH
3 Ph CH
3
30 F Cl O C
2H
5 Ph-4-Cl H
31 F Cl O H H SCH
3
32 F Cl O CN H H
33 F Cl O Ph-4-Cl H H
34 F Cl O CH
2Ph-4-Cl H H
35 F Cl O 3-Py H H
36 F Cl SCH
2CO
2 H H H
37 F Cl SCH
2CO
2 CH
3 H H
38 F Cl SCH
2CO
2 H CH
3 CH
3
39 F Cl SCH
2CO
2 CH
3 Ph CH
3
40 F Cl SCH
2CO
2 C
2H
5 Ph-4-Cl H
41 F Cl SCH
2CO
2 H H SCH
3
42 F Cl SCH
2CO
2 CN H H
43 F Cl SCH
2CO
2 Ph-4-Cl H H
44 F Cl SCH
2CO
2 CH
2Ph-4-Cl H H
45 F Cl SCH
2CO
2 3-Py H H
46 F H SCH(CH
3)CO
2 H H H
47 F Cl S H H H
48 F Cl CH＝C(Cl)CO
2 CN H H
49 F Cl CH
2CH(Cl)CO
2 CN H H
50 F Cl CH＝C(Cl)CO
2 CH
3 H H
51 F Cl CH
2CH(Cl)CO
2 CH
3 H H
52 Cl Cl O H H H
53 Cl Cl OCH
2CO
2 H H H
54 Cl Cl OCH(CH
3)CO
2 H H H
55 Cl Cl CH＝C(Cl)CO
2 H H H
56 Cl Cl CH
2CH(Cl)CO
2 H H H
57 Cl Cl CH
2CH(Cl)CO
2 CH
3 H H
58 Cl Cl SCH
2CO
2 H H H
59 Cl Cl SCH(CH
3)CO
2 H H H
60 Cl Cl CO
2 H H H
61 H Cl O H H H
62 H Cl OCH
2CO
2 H H H
63 H Cl OCH(CH
3)CO
2 H H H
64 H Cl CH＝C(Cl)CO
2 H H H
65 H Cl CH
2CH(Cl)CO
2 H H H
66 H Cl S H H H
67 H Cl SCH
2CO
2 H H H
68 H Cl SCH(CH
3)CO
2 H H H
69 H Cl CH＝C(Cl)CO
2 H H H
70 H Cl CH
2CH(Cl)CO
2 H H H
71 H Cl CO
2 H H H
72 F Cl OCH
2CONH H H H
73 F Cl SCH
2CONH H H H
Table 2
In the compound general formula I: A=N, B=CR
10, Q=Q1No R
1R
2X R
3R
4R
5F
1074 F Cl CO
2H H H H75 F Cl CO
2CH
3H H H76 F Cl CO
2H Cl Cl CO
2CH
377 F Cl CO
2H CH
3CH
3H78 F Cl CO
2C
2H
5Ph-4-Cl H H79 F Cl CO
2H C
2H
5CO
2Et H80 F Cl OCH
2CO
2H H H H81 F Cl OCH
2CO
2CH
3H H H82 F Cl OCH
2CO
2H Cl Cl CO
2CH
383 F Cl OCH (CH
3) CO
2H H H H84 F Cl OCH (CH
3) CO
2CH
3H H H85 F Cl OCH (CH
3) CO
2H Cl Cl CO
2CH
386 F Cl OCH (CH
3) CO
2H CH
3CH
3H87 F Cl OCH (CH
3) CO
2CH
3Ph CH
3H88 F Cl O H H H H89 F Cl O H Cl Cl CO
2CH
390 F Cl SCH
2CO
2H H H H91 F Cl SCH
2CO
2C
2H
5H H H92 F Cl SCH
2CO
2H Cl Cl CO
2CH
393 F Cl SCH
2CO
2H CH
3CH
3H 94 F Cl SCH
2CO
2CN H H H 95 F Cl SCH (CH
3) CO
2H H H H 96 F Cl S H H H H 97 F Cl CH=C (Cl) CO
2H H H H 98 F Cl CH
2CH (Cl) CO
2H H H H 99 Cl Cl O H H H H100 Cl Cl OCH
2CO
2H H H H101 Cl Cl S H H H H102 Cl Cl SCH
2CO
2H H H H103 Cl Cl SCH (CH
3) CO
2H H H H104 Cl Cl CO
2H H H H105 H Cl O H H H H106 H Cl OCH
2CO
2H H H H107 H Cl S H H H H108 H Cl SCH
2CO
2H H H H109 H Cl CO
2H H H H
Table 3
In the compound general formula I: A=CH, B=N, Q=Q1No R
1R
2X R
3R
4R
5110 F Cl CO
2H H H111 F Cl CO
2C
2H
5H H112 F Cl CO
2H Cl Cl113 F Cl OCH
2CO
2H H H114 F Cl OCH
2CO
2CH
3H H115 F Cl OCH
2CO
2CN H H116 F Cl OCH
2CO
2Ph H H117 F Cl SCH
2CO
2H H H118 F Cl SCH
2CO
2CH
3H H119 F Cl SCH (CH
3) CO
2H H H120 F Cl SCH (CH
3) CO
2C
2H
5H H121 F Cl CH=C (Cl) CO
2H H H122 F Cl CH
2CH (Cl) CO
2H H H123 Cl Cl O H H H124 Cl Cl OCH
2CO
2H H H125 Cl Cl S H H H126 Cl Cl SCH
2CO
2H H H127 Cl Cl SCH (CH
3) CO
2H H H128 Cl Cl CO
2H H H129 H Cl O H H H130 H Cl OCH
2CO
2H H H131 H Cl S H H H132 H Cl SCH
2CO
2H H H133 H Cl CO
2H H H
Table 4
Zai compound general formula I Zhong: A=B=N, R4＝R
5＝H，Q＝Q2
No R
1 R
2 X R
3
134 F Cl CO
2 H
135 F Cl CO
2 C
2H
5
136 F Cl CO
2 CN
137 F Cl CO
2 3-Py
138 F Cl OCH
2CO
2 H
139 F Cl OCH
2CO
2 CN
140 F Cl OCH
2CO
2 3-Py
141 F Cl OCH(CH
3)CO
2 H
142 F Cl OCH(CH
3)CO
2 CH
3
143 F Cl CH＝C(Cl)CO
2 H
144 F Cl CH
2CH(Cl)CO
2 H
145 F Cl O H
146 F Cl O CH
3
147 F Cl O CH
2Ph
148 F Cl CH＝C(Cl)CO
2 CN
149 F Cl CH
2CH(Cl)CO
2 CN
150 F Cl O 3-Py
151 F Cl SCH
2CO
2 H
152 F Cl SCH
2CO
2 CN
153 F Cl SCH
2CO
2 3-Py
154 F H SCH(CH
3)CO
2 H
155 F Cl S H
156 Cl Cl O H
157 Cl Cl OCH
2CO
2 H
158 Cl Cl OCH(CH
3)CO
2 H
159 Cl Cl CH＝C(Cl)CO
2 H
160 Cl Cl CH
2CH(Cl)CO
2 H
161 Cl Cl S H
162 Cl Cl SCH
2CO
2 H
163 Cl Cl SCH(CH
3)CO
2 H
164 Cl Cl CO
2 H
165 H Cl O H
166 H Cl OCH
2CO
2 H
167 H Cl OCH(CH
3)CO
2 H
168 H Cl CH＝C(Cl)CO
2 H
169 H Cl CH
2CH(Cl)CO
2 H
170 H Cl S H
171 H Cl SCH
2CO
2 H
172 H Cl SCH(CH
3)CO
2 H
173 H Cl CH＝C(Cl)CO
2 H
174 H Cl CH
2CH(Cl)CO
2 H
175 H Cl CO
2 H
176 F Cl OCH
2CO
2 Ph-4-F
177 F Cl SCH
2CO
2 Ph-4-F
Zai compound general formula I Zhong: A=N, B=CH, R4＝R
5＝CH
3，Q＝Q2
NO R
1 R
2 X R
3
178 F Cl CO
2 H
179 F Cl CO
2 CN
180 F Cl CO
2 3-Py
181 F Cl OCH
2CO
2 H
182 F Cl OCH
2CO
2 C
2H
5
183 F Cl OCH
2CO
2 Ph-4-Cl
184 F Cl OCH
2CO
2 CH
2Ph-4-Cl
185 F Cl OCH
2CO
2 3-Py
186 F Cl OCH(CH
3)CO
2 H
187 F Cl OCH(CH
3)CO
2 C
2H
5
188 F Cl OCH(CH
3)CO
2 CN
189 F Cl OCH(CH
3)CO
2 3-Py
190 F Cl O H
191 F Cl SCH
2CO
2 H
192 F Cl SCH(CH
3)CO
2 CH
3
193 F Cl SCH(CH
3)CO
2 C
2H
5
194 F Cl S H
195 F Cl S CH
3
196 F Cl S C
2H
5
197 Cl Cl O H
198 Cl Cl OCH
2CO
2 H
199 Cl Cl S H
200 Cl Cl SCH
2CO
2 H
201 Cl Cl SCH(CH
3)CO
2 H
202 Cl Cl CO
2 H
203 H Cl O H
204 H Cl OCH
2CO
2 H
205 H Cl S H
206 H Cl SCH
2CO
2 H
207 H Cl CO
2 H
Table 6
In the compound general formula I: A=CH, B=N, R
4=R
5=H, Q=Q2 No R
1R
2X R
2208 F Cl CO
2H209 F Cl CO
2C
2H
5210 F Cl CO
2Ph211 F Cl CO
2CH
2Ph-4-Cl212 F Cl CO
23-Py213 F Cl OCH
2CO
2H214 F Cl OCH
2CO
2CH
2Ph-4-Cl215 F Cl OCH
2CO
23-Py216 F Cl OCH (CH
3) CO
2H217 F Cl OCH (CH
3) CO
2CH
3218 F Cl O H219 F Cl O CH
3220 F Cl SCH
2CO
2H221 Cl Cl O H222 Cl Cl OCH
2CO
2H223 Cl Cl S H224 Cl Cl SCH
2CO
2H225 Cl Cl SCH (CH
3) CO
2H226 Cl Cl CO
2227 H Cl O228 H Cl OCH
2CO
2229 H Cl S230 H Cl SCH
2CO
2231 H Cl CO
2
Table 7
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q3NO R
1R
2X R
3232 F Cl CO
2H233 F Cl CO
2CH
3234 F Cl CO
2CN235 F Cl CO
23-Py236 F Cl OCH
2CO
2H237 F Cl OCH (CH
3) CO
2CN238 F Cl OCH (CH
3) CO
23-Py239 F Cl SCH
2CO
2H240 F Cl CH=C (Cl) CO
2H241 F Cl CH
2CH (Cl) CO
2H242 Cl Cl OCH
2CO
2H243 Cl Cl CH=C (Cl) CO
2H244 Cl Cl CH
2CH (Cl) CO
2H245 Cl Cl SCH
2CO
2H246 Cl Cl CO
2H247 H Cl OCH
2CO
2H248 H Cl CH=C (Cl) CO
2H249 H Cl CH
2CH (Cl) CO
2H250 H Cl SCH
2CO
2H251 H Cl CO
2H252 F Cl OCH
2CO
2Ph-4-F253 F Cl SCH
2CO
2Ph-4-F
Table 8
In the compound general formula I: A=N, B=CH, R
4=R
5=CH
3, Q=Q3No R
1R
2X R
3254 F Cl CO
2H255 F Cl OCH
2CO
2H256 F Cl SCH
2CO
2H
Table 9
In the compound general formula I: A=CH, B=N, R
4=R
5=H, Q=Q3 NO R
1R
2X R
3257 F Cl CO
2H258 F Cl CO
2C
2H
5259 F Cl CO
2Ph260 F Cl CO
2CH
2Ph-4-Cl261 F Cl CO
23-Py262 F Cl OCH
2CO
2H263 F Cl OCH
2CO
2CH
2Ph-4-Cl264 F Cl OCH
2CO
23-Py265 F Cl SCH
2CO
2H266 F Cl SCH
2CO
2CH
3267 F Cl SCH
2CO
2C
2H
5268 F Cl SCH
2CO
2Ph269 F Cl SCH
2CO
2CH
2Ph270 F Cl SCH
2CO
2Ph-4-Cl271 F Cl SCH
2CO
2CH
2Ph-4-Cl272 F Cl SCH
2CO
23-Py
Table 10
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q4 No R
1R
2X R
2273 F Cl CO
2H274 F Cl CO
2CH
3275 F Cl CO
2CN276 F Cl CO
23-Py277 F Cl OCH
2CO
2H278 F Cl OCH
2CO
23-Py279 F Cl SCH
2CO
2CH
3280 F Cl SCH
2CO
2C
2H
5281 F Cl SCH
2CO
2CN282 F Cl SCH
2CO
23-Py283 F Cl CH=C (Cl) CO
2CN284 F Cl CH
2CH (Cl) CO
2CN285 F Cl CH=C (Cl) CO
2H286 F Cl CH
2CH (Cl) CO
2H287 Cl Cl OCH
2CO
2H288 Cl Cl OCH (CH
3) CO
2H289 Cl Cl SCH
2CO
2H290 Cl Cl CH=C (Cl) CO
2H291 Cl Cl CH
2CH (Cl) CO
2H292 Cl Cl CO
2H293 H Cl OCH
2CO
2H294 H Cl OCH (CH
3) CO
2H295 H Cl SCH
2CO
2H296 H Cl CH=C (Cl) CO
2H297 H Cl CH
2CH (Cl) CO
2H298 H Cl CO
2H299 F Cl OCH
2CO
2Ph-4-F300 F Cl SCH
2CO
2Ph-4-F
Table 11
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q5 No R
1R
2X R
3301 F Cl CO
2H302 F Cl CO
2CH
3303 F Cl CO
2Ph-4-Cl304 F Cl CO
2CN305 F Cl CO
23-Py306 F Cl OCH
2CO
2H307 F Cl OCH
2CO
2Ph-4-Cl308 F Cl OCH
2CO
2CN309 F Cl SCH
2CO
2H310 F Cl SCH
2CO
2CH
3311 F Cl SCH
2CO
2C
2H
5312 F Cl CH=C (Cl) CO
2H313 F Cl CH
2CH (Cl) CO
2H314 Cl Cl OCH
2CO
2H315 Cl Cl OCH (CH
3) CO
2H316 Cl Cl SCH
2CO
2H317 Cl Cl CH=C (Cl) CO
2H318 Cl Cl CH
2CH (Cl) CO
2H319 Cl Cl CO
2H320 H Cl OCH
2CO
2H321 H Cl OCH (CH
3) CO
2H322 H Cl SCH
2CO
2H323 H Cl CH=C (Cl) CO
2H324 H Cl CH
2CH (Cl) CO
2H325 H Cl CO
2H326 F Cl OCH
2CO
2Ph-4-F327 F Cl SCH
2CO
2Ph-4-F
Table 12
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q6 No R
1R
2X R
3328 F Cl CO
2H329 F Cl OCH
2CO
2H330 F Cl OCH
2CO
2CH
3331 F Cl O H332 F Cl O CH
3333 F Cl O C
2H
5334 F Cl O CN335 F Cl O 3-Py336 F Cl SCH
2CO
2H337 F Cl SCH
2CO
2CH
3338 F Cl SCH
2CO
2C
2H
5339 F Cl CH=C (Cl) CO
2H340 F Cl CH
2CH (Cl) CO
2H 341 Cl Cl O H 342 Cl Cl OCH
2CO
2H 343 Cl Cl CH=C (Cl) CO
2H 344 Cl Cl CH
2CH (Cl) CO
2H 345 Cl Cl SCH
2CO
2H 346 Cl Cl SCH (CH
3) CO
2H 347 Cl Cl CO
2H 348 H Cl O H 349 H Cl OCH
2CO
2H 350 H Cl OCH (CH
3) CO
2H 351 H Cl SCH
2CO
2H 352 H Cl CH=C (Cl) CO
2H 353 H Cl CH
2CH (Cl) CO
2H 354 H Cl CO
2H 355 F Cl OCH
2CO
2Ph-4-F 356 F Cl SCH
2CO
2Ph-4-F
Table 13
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q7 No R
1R
2X R
3357 F Cl CO
2H358 F Cl OCH
2CO
2H359 F Cl OCH
2CO
2CH
3360 F Cl O H361 F Cl O CH
3362 F Cl SCH
2CO
2H363 F Cl SCH
2CO
2CH
3364 F Cl CH=C (Cl) CO
2H365 F Cl CH
2CH (Cl) CO
2H366 Cl Cl O H367 Cl Cl OCH2CO
2H368 Cl Cl CH=C (Cl) CO
2H369 Cl Cl CH
2CH (Cl) CO
2H370 Cl Cl SCH
2CO
2H371 Cl Cl SCH (CH
3) CO
2H372 Cl Cl CO
2H373 H Cl O H374 H Cl OCH
2CO
2H375 H Cl OCH (CH
3) CO
2H376 H Cl SCH
2CO
2H377 H Cl CH=C (Cl) CO
2H378 H Cl CH
2CH (Cl) CO
2H379 H Cl CO
2H380 F Cl OCH
2CO
2Ph-4-F381 F Cl SCH
2CO
2Ph-4-F
Table 14
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q8 NO R
1R
2X R
3382 F Cl CO
2H383 F Cl OCH
2CO
2H384 F Cl OCH
2CO
2CH
3385 F Cl O Ph386 F Cl O CH
2Ph387 F Cl SCH
2CO
2CH
3388 F Cl SCH
2CO
2C
2H
5389 F Cl CH=C (Cl) CO
2H390 F Cl CH
2CH (Cl) CO
2H391 Cl Cl O H392 Cl Cl OCH
2CO
2H393 Cl Cl CH=C (Cl) CO
2H394 Cl Cl CH
2CH (Cl) CO
2H395 Cl Cl SCH
2CO
2H396 Cl Cl SCH (CH
3) CO
2H397 Cl Cl CO
2H398 H Cl O H399 H Cl OCH
2CO
2H400 H Cl OCH (CH
3) CO
2H401 H Cl SCH
2CO
2H402 H Cl CH=C (Cl) CO
2H403 H Cl CH
2CH (Cl) CO
2H404 H Cl CO
2H405 F Cl OCH
2CO
2Ph-4-F406 F Cl SCH
2CO
2Ph-4-F
Table 15
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q9 No R
1R
2X R
3407 F Cl CO
2H408 F Cl OCH
2CO
2H409 F Cl O 3-Py410 F Cl SCH
2CO
2H411 F Cl SCH
2CO
2CH
3412 F H SCH (CH
3) CO
2H413 F Cl SCH (CH
3) CO
2CH
3414 F Cl CH=C (Cl) CO
2H415 F Cl CH
2CH (Cl) CO
2H416 Cl Cl O H417 Cl Cl OCH
2CO
2H418 Cl Cl CH=C (Cl) CO
2H419 Cl Cl CH
2CH (Cl) CO
2H420 Cl Cl SCH
2CO
2H421 Cl Cl SCH (CH
3) CO
2H422 Cl Cl CO
2H423 H Cl O H424 H Cl OCH
2CO
2H425 H Cl OCH (CH
3) CO
2H426 H Cl SCH
2CO
2H427 H Cl CH=C (Cl) CO
2H428 H Cl CH
2CH (Cl) CO
2H429 H Cl CO
2H430 F Cl OCH
2CO
2Ph-4-F431 F Cl SCH
2CO
2Ph-4-F
Table 16
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q10 NO R
1R
2X R
3432 F Cl CO
2H433 F Cl OCH
2CO
2H434 F Cl OCH
2CO
2CH
3435 F Cl O 3-Py436 F Cl SCH
2CO
2H437 F Cl SCH
2CO
2CH
3438 F Cl CH=C (Cl) CO
2H439 F Cl CH
2CH (Cl) CO
2H440 Cl Cl O H441 Cl Cl OCH
2CO
2H442 Cl Cl CH=C (Cl) CO
2H443 Cl Cl CH
2CH (Cl) CO
2H444 Cl Cl SCH
2CO
2H445 Cl Cl SCH (CH
3) CO
2H446 Cl Cl CO
2H447 H Cl O H448 H Cl OCH
2CO
2H449 H Cl OCH (CH
3) CO
2H450 H Cl SCH
2CO
2H451 H Cl CH=C (Cl) CO
2H452 H Cl CH
2CH (Cl) CO
2H453 H Cl CO
2H454 F Cl OCH
2CO
2Ph-4-F455 F Cl SCH
2CO
2Ph-4-F
Table 17
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q11 No R
1R
2X R
3456 F Cl CO
2H457 F Cl OCH
2CO
2H458 F Cl SCH
2CO
2H459 F Cl CH=C (Cl) CO
2H460 F Cl CH
2CH (Cl) CO
2H461 Cl Cl O H462 Cl Cl OCH
2CO
2H463 Cl Cl CH=C (Cl) CO
2H464 Cl Cl CH
2CH (Cl) CO
2H465 Cl Cl SCH
2CO
2H467 Cl Cl SCH (CH
3) CO
2H468 Cl Cl CO
2H469 H Cl O H470 H Cl OCH
2CO
2H471 H Cl OCH (CH
3) CO
2H472 H Cl SCH
2CO
2H473 H Cl CH=C (Cl) CO
2H474 H Cl CH
2CH (Cl) CO
2H475 H Cl CO
2H476 F Cl OCH
2CO
2Ph-4-F477 F Cl SCH
2CO
2Ph-4-F
Table 18
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q12 No R
1R
2X R
3R
10478 F Cl CO
2H CH
3479 F Cl CO
2H NH
2480 F Cl OCH
2CO
2H CH
3481 F Cl OCH
2CO
2CH
3CH
3482 F Cl OCH
2CO
2H NH
2483 F Cl OCH (CH
3) CO
2CN NH
2484 F Cl O H H485 F Cl O H CH
3486 F Cl O CH
3X CH
3487 F Cl O C
2H
5CH
3488 F Cl SCH
2CO
2H CH
3489 F Cl CH=C (Cl) CO
2H NH
2490 F Cl CH
2CH (Cl) CO
2H NH
2491 F Cl CH=C (Cl) CO
2CN NH
2492 F Cl CH
2CH (Cl) CO
2CN NH
2493 F Cl S H CH
3494 F Cl S H NH
2495 F Cl CH=C (Cl) CO
2H CH
3496 F Cl CH
2CH (Cl) CO
2H CH
3497 F Cl CH=C (Cl) CO
2CN CH
3498 F Cl CH
2CH (Cl) CO
2CN CH
3499 Cl Cl O H NH
2500 Cl Cl OCH
2CO
2H CH
3501 Cl Cl OCH (CH
3) CO
2H CH
3502 Cl Cl SCH
2CO
2H CH
3503 Cl Cl CH=C (Cl) CO
2H CH
3504 Cl Cl CH
2CH (Cl) CO
2H CH
3505 Cl Cl CO
2H CH
3506 H Cl O H CH
3507 H Cl OCH
2CO
2H CH
3508 H Cl OCH (CH
3) CO
2H CH
3509 H Cl SCH
2CO
2H CH
3510 H Cl CH=C (Cl) CO
2H NH
2511 H Cl CH
2CH (Cl) CO
2H NH
2512 H Cl CO
2H NH
2513 H Cl OCH
2CO
2H NH
2514 H Cl SCH
2CO
2H NH
2
Table 19
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q13 No R
1R
2X R
3R
10515 F Cl CO
2H CH
3516 F Cl CO
2CH
3NH
2517 F Cl CO
2C
2H
5NH
2518 F Cl OCH
2CO
2H CH
3519 F Cl OCH
2CO
2CH
3CH
3520 F Cl OCH
2CO
2CH
3NH
2521 F Cl OCH
2CO
2C
2H
5NH
2522 F Cl O CH
3NH
2523 F Cl O C
2H
5NH
2524 F Cl SCH
2CO
2C
2H
5CH
3525 F Cl SCH
2CO
2H NH
2526 F Cl CH=C (Cl) CO
2H CH
3527 F Cl CH
2CH (Cl) CO
2H CH
3528 F Cl CH=C (Cl) CO
2CN CH
3529 F Cl CH
2CH (Cl) CO
2CN CH
3530 Cl Cl O H NH
2531 Cl Cl OCH
2CO
2H CH
3532 Cl Cl OCH (CH
3) CO
2H CH
3533 Cl Cl SCH
2CO
2H CH
3534 Cl Cl CH=C (Cl) CO
2H CH
3535 Cl Cl CH
2CH (Cl) CO
2H CH
3536 Cl Cl CO
2H CH
3537 H Cl O H CH
3538 H Cl OCH
2CO
2H CH
3539 H Cl OCH (CH
3) CO
2H CH
3540 H Cl SCH
2CO
2H CH
3541 H Cl CH=C (Cl) CO
2H NH
2542 H Cl CH
2CH (Cl) CO
2H NH
2543 H Cl CO
2H NH
2544 H Cl OCH
2CO
2H NH
2545 H Cl SCH
2CO
2H NH
2
Table 20
In the compound general formula I: A=B=N, R
4=R
5=H, R
11=CH
3, Q=Q14 No R
1R
2X R
3R
10546 F Cl CO
2H CH
3547 F Cl CO
2CH
3CH
3548 F Cl CO
2C
2H
5NH
2549 F Cl OCH
2CO
2H CH
3550 F Cl O H CH
3551 F Cl O C
2H
5NH
2552 F Cl O CN NH
2553 F Cl O CN CH
3554 F Cl SCH
2CO
2H CH
3555 F Cl SCH
2CO
2CH
3NH
2556 F Cl SCH
2CO
2C
2H
5NH
2557 F Cl SCH
2CO
2CN NH
2558 F Cl SCH
2CO
2CN CH
3559 F Cl CH=C (Cl) CO
2H NH
2560 F Cl CH
2CH (Cl) CO
2H NH
2561 F Cl CH=C (Cl) CO
2CN NH
2562 F Cl CH
2CH (Cl) CO
2CN NH
2563 F Cl S H CH
3564 F Cl S H NH
2565 F Cl CH=C (Cl) CO
2H CH
3566 F Cl CH
2CH (Cl) CO
2H CH
3567 F Cl CH=C (Cl) CO
2CN CH
3568 F Cl CH
2CH (Cl) CO
2CN CH
3569 Cl Cl O H NH
2570 Cl Cl OCH
2CO
2H CH
3571 Cl Cl OCH (CH
3) CO
2H CH
3572 Cl Cl SCH
2CO
2H CH
3573 Cl Cl CH=C (Cl) CO
2H CH
3574 Cl Cl CH
2CH (Cl) CO
2H CH
3575 Cl Cl CO
2H CH
3576 H Cl O H CH
3577 H Cl OCH
2CO
2H CH
3578 H Cl OCH (CH
3) CO
2H CH
3579 H Cl SCH
2CO
2H CH
3580 H Cl CH=C (Cl) CO
2H NH
2581 H Cl CH
2CH (Cl) CO
2H NH
2582 H Cl CO
2H NH
2583 H Cl OCH
2CO
2H NH
2584 H Cl SCH
2CO
2H NH
2
Table 21
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q15No R
1R
2X R
3R
10585 F Cl CO
2H CH
3586 F Cl CO
2C
2H
5NH
2587 F Cl OCH
2CO
2H CH
3588 F Cl O C
2H
5NH
2589 F Gl O CN NH
2590 F Cl SCH
2CO
2CH
3CH
3591 F Cl CH=C (Cl) CO
2H NH
2592 F Cl CH
2CH (Cl) CO
2H NH
2593 F Cl CH=C (Cl) CO
2CN NH
2594 F Cl CH
2CH (Cl) CO
2CN NH
2595 F Cl S H CH
3596 F Cl S H NH
2597 F Cl CH=C (Cl) CO
2H CH
3598 F Cl CH
2CH (Cl) CO
2H CH
3599 F Cl CH=C (Cl) CO
2CN CH
3600 F Cl CH
2CH (Cl) CO
2CN CH
3601 Cl Cl O H NH
2602 Cl Cl OCH
2CO
2H CH
3603 Cl Cl OCH (CH
3) CO
2H CH
3604 Cl Cl SCH
2CO
2H CH
3605 Cl Cl CH=C (Cl) CO
2H CH
3606 CI Cl CH
2CH (Cl) CO
2H CH
3607 CI Cl CO
2H CH
3608 H Cl O H CH
3609 H Cl OCH
2CO
2H CH
3610 H Cl OCH (CH
3) CO
2H CH
3611 H Cl SCH
2CO
2H CH
3612 H Cl CH=C (Cl) CO
2H NH
2613 H Cl CH
2CH (CI) CO
2H NH
2614 H Cl CO
2H NH
2615 H Cl OCH
2CO
2H NH
2616 H Cl SCH
2CO
2H NH
3
Table 22
In the compound general formula I: A=B=N, R
4=R
5=H, Q=Q16 No R
1R
2X R
3617 F Cl CO
2H618 F Cl OCH
2CO
2H619 F Cl OCH
2CO
2CH
3620 F Cl O H621 F Cl SCH
2CO
2H622 F Cl CH=C (Cl) CO
2H623 F Cl CH
2CH (Cl) CO
2H624 Cl Cl O H625 Cl Cl OCH
2CO
2H626 Cl Cl CH=C (Cl) CO
2H627 Cl Cl CH
2CH (Cl) CO
2H628 Cl Cl SCH
2CO
2H629 Cl Cl SCH (CH
3) CO
2H630 Cl Cl CO
2H631 H Cl O H632 H Cl OCH
2CO
2H633 H Cl OCH (CH
3) CO
2H634 H Cl SCH
2CO
2H635 H Cl CH=C (Cl) CO
2H636 H Cl CH
2CH (Cl) CO
2H637 H Cl CO
2H638 F Cl OCH
2CO
2Ph-4-F639 F Cl SCH
2CO
2Ph-4-F
Table 23Zai compound general formula I Zhong: A=R4＝R
5＝H，A＝B＝N，R
10＝CH
3，R
11＝CH
3，Z＝O
No R
1 R
2 X Q
640 F Cl OCH
2CO Q1
641 F Cl OCH
2CO Q2
642 F Cl OCH
2CO Q3
643 F Cl OCH
2CO Q4
644 F Cl OCH
2CO Q5
645 F Cl OCH
2CO Q6
646 F Cl OCH
2CO Q7
647 F Cl OCH
2CO Q8
648 F Cl OCH
2CO Q9
649 F Cl OCH
2CO Q10
650 F Cl OCH
2CO Q11
651 F Cl OCH
2CO Q12
652 F Cl OCH
2CO Q13
653 F Cl OCH
2CO Q14
654 F Cl OCH
2CO Q16
655 F Cl CH＝C(Cl)CO Q1
656 F Cl CH＝C(Cl)CO Q2
657 F Cl CH＝C(Cl)CO Q3
658 F Cl CH＝C(Cl)CO Q4
659 F Cl CH＝C(Cl)CO Q5
660 F Cl CH＝C(Cl)CO Q6
661 F Cl CH＝C(Cl)CO Q7
662 F Cl CH＝C(Cl)CO Q8
663 F Cl CH＝C(Cl)CO Q9
664 F Cl CH＝C(Cl)CO Q10
665 F Cl CH＝C(Cl)CO Q11
666 F Cl CH＝C(Cl)CO Q12
667 F Cl CH＝C(Cl)CO Q13
668 F Cl CH＝C(Cl)CO Q14
669 F Cl CH＝C(Cl)CO Q16
670 F Cl CO Q1
671 F Cl CO Q2
672 F Cl CO Q3
673 F Cl CO Q4
674 F Cl CO Q5
675 F Cl CO Q6
676 F Cl CO Q7
677 F Cl CO Q8
678 F Cl CO Q9
679 F Cl CO Q10
680 F Cl CO Q11
681 F Cl CO Q12
682 F Cl CO Q13
683 F Cl CO Q14
684 F Cl CO Q16
685 F Cl SCH
2CO Q1
686 F Cl SCH
2CO Q2
687 F Cl SCH
2CO Q3
688 F Cl SCH
2CO Q4
689 F Cl SCH
2CO Q5
690 F Cl SCH
2CO Q6
691 F Cl SCH
2CO Q7
692 F Cl SCH
2CO Q8
693 F Cl SCH
2CO Q9
694 F Cl SCH
2CO Q10
695 F Cl SCH
2CO Q11
696 F Cl SCH
2CO Q12
697 F Cl SCH
2CO Q13
698 F Cl SCH
2CO Q14
699 F Cl SCH
2CO Q16
700 Cl Cl CH＝C(Cl)CO Q1
701 Cl Cl CH＝C(Cl)CO Q3
702 Cl Cl CH＝C(Cl)CO Q6
703 Cl Cl CH＝C(Cl)CO Q7
704 Cl Cl CH＝C(Cl)CO Q8
705 Cl Cl CH＝C(Cl)CO Q10
706 Cl Cl CH＝C(Cl)CO Q11
707 Cl Cl CH＝C(Cl)CO Q12
708 Cl Cl CH＝C(Cl)CO Q16
709 Cl Cl OCH
2CO Q1
710 Cl Cl OCH
2CO Q3
711 Cl Cl OCH
2CO Q6
712 Cl Cl OCH
2CO Q7
713 Cl Cl OCH
2CO Q8
714 Cl Cl OCH
2CO Q10
715 Cl Cl OCH
2CO Q11
716 Cl Cl OCH
2CO Q12
717 Cl Cl OCH
2CO Q16
718 Cl Cl SCH
2CO Q1
719 Cl Cl SCH
2CO Q3
720 Cl Cl SCH
2CO Q6
721 Cl Cl SCH
2CO Q7
722 Cl Cl SCH
2CO Q8
723 Cl Cl SCH
2CO Q10
724 Cl Cl SCH
2CO Q11
725 Cl Cl SCH
2CO Q12
726 Cl Cl SCH
2CO Q16
727 Cl Cl CO Q1
728 Cl Cl CO Q3
729 Cl Cl CO Q6
730 Cl Cl CO Q7
731 Cl Cl CO Q8
732 Cl Cl CO Q10
733 Cl Cl CO Q11
734 Cl Cl CO Q12
735 Cl Cl CO Q16
736 H Cl CH＝C(Cl)CO Q1
737 H Cl CH＝C(Cl)CO Q3
738 H Cl CH＝C(Cl)CO Q6
739 H Cl CH＝C(Cl)CO Q7
740 H Cl CH＝C(Cl)CO Q8
741 H Cl CH＝C(Cl)CO Q10
742 H Cl CH＝C(Cl)CO Q11
743 H Cl CH＝C(Cl)CO Q12
744 H Cl CH＝C(Cl)CO Q16
745 H Cl OCH
2CO Q1
746 H Cl OCH
2CO Q3
747 H Cl OCH
2CO Q6
748 H Cl OCH
2CO Q7
749 H Cl OCH
2CO Q8
750 H Cl OCH
2CO Q10
751 H Cl OCH
2CO Q11
752 H Cl OCH
2CO Q12
753 H Cl OCH
2CO Q16
754 H Cl SCH
2CO Q1
755 H Cl SCH
2CO Q3
756 H Cl SCH
2CO Q6
757 H Cl SCH
2CO Q7
758 H Cl SCH
2CO Q8
759 H Cl SCH
2CO Q10
760 H Cl SCH
2CO Q11
761 H Cl SCH
2CO Q12
762 H Cl SCH
2CO Q16
763 H Cl CO Q1
764 H Cl CO Q3
765 H Cl CO Q6
766 H Cl CO Q7
767 H Cl CO Q8
768 H Cl CO Q10
769 H Cl CO Q11
770 H Cl CO Q12
771 H Cl CO Q16
Table 24
Zai compound general formula I Zhong: R3＝R
4＝R
5＝H，A＝B＝N，R
10＝CH
3 No R
1 R
2 X Q Salt
772 F Cl O Q1 HCl
773 F Cl OCH
2CO
2 Q1 HCl
774 F Cl SCH
2CO
2 Q1 HCl
775 F Cl CO
2 Q1 HCl
776 F Cl CH
2CH(Cl)CO
2 Q1 HCl
777 F Cl CH＝C(Cl)CO
2 Q1 HCl
778 F Cl OCH
2CO
2 Q1 H
3PO
4
779 F Cl OCH
2CO
2 Q1 CH
3CO
2H
780 F Cl OCH
2CO
2 Q1 HCO
2CO
2H
781 F Cl SCH
2CO
2 Q1 HCO
2CO
2H
782 F Cl CO
2 Q1 HCO
2CO
2H
783 F Cl CH
2CH(Cl)CO
2 Q1 HCO
2CO
2H
784 F Cl CH＝C(Cl)CO
2 Q1 HCO
2CO
2H
785 Cl Cl O Q1 HCl
786 Cl Cl OCH
2CO
2 Q1 HCl
787 Cl Cl SCH
2CO
2 Q1 HCl
788 Cl Cl CO
2 Q1 HCl
789 Cl Cl CH
2CH(Cl)CO
2 Q1 HCl
790 Cl Cl CH＝C(Cl)CO
2 Q1 HCl
791 Cl Cl O Q1 HCO
2CO
2H
792 Cl Cl OCH
2CO
2 Q1 HCO
2CO
2H
793 Cl Cl SCH
2CO
2 Q1 HCO
2CO
2H
794 Cl Cl CO
2 Q1 HCO
2CO
2H
795 Cl Cl CH
2CH(Cl)CO
2 Q1 HCO
2CO
2H
796 Cl Cl CH＝C(Cl)CO
2 Q1 HCO
2CO
2H
797 H Cl O Q1 HCl
798 H Cl OCH
2CO
2 Q1 HCl
799 H Cl SCH
2CO
2 Q1 HCl
800 H Cl CO
2 Q1 HCl
801 H Cl CH
2CH(Cl)CO
2 Q1 HCl
802 H Cl CH＝C(Cl)CO
2 Q1 HCl
803 H Cl O Q1 HCO
2CO
2H
804 H Cl OCH
2CO
2 Q1 HCO
2CO
2H
805 H Cl SCH
2CO
2 Q1 HCO
2CO
2H
806 H Cl CO
2 Q1 HCO
2CO
2H
807 H Cl CH
2CH(Cl)CO
2 Q1 HCO
2CO
2H
808 H Cl CH＝C(Cl)CO
2 Q1 HCO
2CO
2H
809 F Cl O Q3 HCl
810 F Cl OCH
2CO
2 Q3 HCl
811 F Cl SCH
2CO
2 Q3 HCl
812 F Cl CO
2 Q3 HCl
813 F Cl CH
2CH(Cl)CO
2 Q3 HCl
814 F Cl CH＝C(Cl)CO
2 Q3 HCl
815 F Cl O Q7 HCl
816 F Cl OCH
2CO
2 Q7 HCl
817 F Cl SCH
2CO
2 Q7 HCl
818 F Cl CO
2 Q7 HCl
819 F Cl CH
2CH(Cl)CO
2 Q7 HCl
820 F Cl CH＝C(Cl)CO
2 Q7 HCl
821 F Cl O Q8 HCl
822 F Cl OCH
2CO
2 Q8 HCl
823 F Cl SCH
2CO
2 Q8 HCl
824 F Cl CO
2 Q8 HCl
825 F Cl CH
2CH(Cl)CO
2 Q8 HCl
826 F Cl CH＝C(Cl)CO
2 Q8 HCl
827 F Cl O Q10 HCl
828 F Cl OCH
2CO
2 Q10 HCl
829 F Cl SCH
2CO
2 Q10 HCl
830 F Cl CO
2 Q10 HCl
831 F Cl CH
2CH(Cl)CO
2 Q10 HCl
832 F Cl CH＝C(Cl)CO
2 Q10 HCl
833 F Cl O Q11 HCl
834 F Cl OCH
2CO
2 Q11 HCl
835 F Cl SCH
2CO
2 Q11 HCl
836 F Cl CO
2 Q11 HCl
837 F Cl CH
2CH(Cl)CO
2 Q11 HCl
838 F Cl CH＝C(Cl)CO
2 Q11 HCl
839 Cl Cl O Q12 HCl
840 Cl Cl OCH
2CO
2 Q12 HCl
841 Cl Cl SCH
2CO
2 Q12 HCl
842 Cl Cl CO
2 Q12 HCl
843 Cl Cl CH
2CH(Cl)CO
2 Q12 HCl
844 Cl Cl CH＝C(Cl)CO
2 Q12 HCl
Table 25
Zai compound general formula I Zhong: R when Q=Q1210＝CH
3 No R
1 R
2 X Z R
4 R
5 Q A B
845 F Cl NH CO H H Q1 N N
846 F Cl NH CO H H Q1 N CH
847 F Cl NH CO CH
3 CH
3 Q1 N CCO
2CH
3
848 F Cl NH CO Cl Cl Q1 N CCONMe
2
849 F Cl NH CO C
2H
5 CO
2CH
3 Q1 N CH
850 F Cl NH CO CH
3 CONHPh Q1 N CH
851 F Cl NH CO Ph-4-Cl CO
2NMe
2 Q1 N CCl
852 F Cl NH CO H H Q1 CH N
853 F Cl NSO
2CH
3 CO H H Q1 N N
854 F Cl NSO
2CH
3 CH
2 H H Q1 N N
855 F Cl NSO
2CH
3 CO H H Q2 N N
856 F Cl NSO
2CH
3 CH
2 H H Q2 N N
857 F CN NSO
2CH
3 CO H H Q3 N CH
858 F Cl NSO
2CH
3 CH
2 H H Q3 N N
859 F Cl NSO
2CH
3 CH
2 H H Q3 N CH
860 F Cl NSO
2CH
3 CO H H Q7 CH N
861 F Cl NSO
2CH
3 CO H H Q7 N N
862 F Cl NSO
2CH
3 CH
2 H H Q7 CH N
863 F Cl NSO
2CH
3 CO H H Q8 N N
864 F Cl NSO
2CF
3 CO H H Q8 N N
865 F Cl NSO
2CF
3 CO H H Q8 CH N
866 F Cl NSO
2Et CO CH
3 CH
3 Q8 CH N
867 F Cl NSO
2Et CO CH
3 CH
3 Q8 N CH
868 Cl Cl NSO
2CH
3 CO H H Q8 N N
869 Cl Cl NSO
2CF
3 CO H H Q8 N N
870 Cl Cl NSO
2CF
3 CO H H Q8 CH N
871 Cl Cl NSO
2CF
3 CO H H Q8 N CH
872 F Cl CH
2C(Cl) CO H H Q8 N N
873 F Cl CH
2C(Cl) CO H H Q8 CH N
874 H Cl CH＝C(Cl) CO H H Q1 N N
875 F Cl OCH
2 CO H H Q1 N N
876 F Cl SCH
2 CO H H Q3 N N
877 F Cl CH
2C(Cl) CO H H Q10 N CH
878 H Cl CH＝C(Cl) CO H H Q10 N N
879 F Cl OCH
2 CO H H Q10 N N
880 F Cl SCH
2 CO H H Q10 N N
881 F Cl CH
2C(Cl) CO H H Q11 N CH
882 H Cl CH＝C(Cl) CO H H Q11 N N
883 F Cl OCH
2 CO H H Q11 N N
884 F Cl SCH
2 CO H H Q11 N N
885 F Cl CH
2C(Cl) CO H H Q12 N CH
886 H Cl CH＝C(Cl) CO H H Q12 N N
887 F Cl OCH
2 CO H H Q12 N N
888 F Cl SCH
2 CO H H Q12 N N
889 F Cl CH
2C(Cl) CO H H Q16 N CH
890 H Cl CH＝C(Cl) CO H H Q16 N N
891 F Cl OCH
2 CO H H Q16 N N
892 F Cl SCH
2 CO H H Q16 N N
893 F Cl NSO
2CH
3 CO H H Q7 N N
894 F Cl NSO
2CH
3 CO H H Q10 N N
895 F Cl NSO
2CH
3 CO H H Q11 N N
896 F Cl NSO
2CH
3 CO H H Q12 N N
897 F Cl NSO
2CH
3 CO H H Q16 N N
898 F Cl NSO
2CH
3 CH
2 H H Q7 N N
899 F Cl NSO
2CH
3 CH
2 H H Q10 N N
900 F Cl NSO
2CH
3 CH
2 H H Q11 N N
901 F Cl NSO
2CH
3 CH
2 H H Q12 N N
902 F Cl NSO
2CH
3 CH
2 H H Q16 N N
903 Cl Cl NSO
2CH
3 CO H H Q7 N N
904 Cl Cl NSO
2CH
3 CO H H Q10 N N
905 Cl Cl NSO
2CH
3 CO H H Q11 N N
906 Cl Cl NSO
2CH
3 CO H H Q12 N N
907 Cl Cl NSO
2CH
3 CO H H Q16 N N
908 Cl Cl NSO
2CH
3 CH
2 H H Q7 N N
909 Cl Cl NSO
2CH
3 CH
2 H H Q10 N N
910 Cl Cl NSO
2CH
3 CH
2 H H Q11 N N
911 Cl Cl NSO
2CH
3 CH
2 H H Q12 N N
912 Cl Cl NSO
2CH
3 CH
2 H H Q16 N N
913 H Cl NSO
2CH
3 CO H H Q7 N N
914 H Cl NSO
2CH
3 CO H H Q10 N N
915 H Cl NSO
2CH
3 CO H H Q11 N N
916 H Cl NSO
2CH
3 CO H H Q12 N N
917 H Cl NSO
2CH
3 CO H H Q16 N N
918 H Cl NSO
2CH
3 CH
2 H H Q7 N N
919 H Cl NSO
2CH
3 CH
2 H H Q10 N N
920 H Cl NSO
2CH
3 CH
2 H H Q11 N N
921 H Cl NSO
2CH
3 CH
2 H H Q12 N N
922 H Cl NSO
2CH
3 CH
2 H H Q16 N N
923 H Cl NSO
2CH
3 CO H H Q8 N N
924 H Cl NSO
2CH
3 CO H H Q8 CH N
925 H Cl NSO
2CH
3 CO H H Q8 N CH
926 H Cl NSO
2CF
3 CO H H Q8 N N
927 H Cl NSO
2CF
3 CO H H Q8 CH N
928 H Cl NSO
2CF
3 CO H H Q8 N CH
929 H Cl NSO
2Et CO CH
3 CH
3 Q8 N N
930 H Cl NSO
2Et CO CH
3 CH
3 Q8 CH N
931 H Cl NSO
2Et CO CH
3 CH
2 Q8 N CH
The present invention also comprises by represented a kind of substituted triazole, imidazoles, pyrazole compound and the agriculture formed herbicidal composition of applicable carrier of with weeding activity of general formula I.
Other embodiments of the present invention are that prevention target crop field is (as wheat, corn and soybean) in method for weed, this method comprises that substituted triazole, imidazoles, the pyrazoles herbicidal composition with compound shown in the general formula I of herbicidally effective amount and acceptable carrier composition imposes on the surface of growth medium of the places of described weeds, described weeds or described weeds.
The expressed compound of general formula I is useful as the effective constituent of weedicide.When the compound of general formula I of the present invention as weedicide, the formulation that effective constituent is fit to depends on specific purposes and suitable application process.In general, effective constituent is dissolved with inert solvent and solid carrier, and applied formulation has pulvis, wettable powder, and missible oil, aqua and oil suspending agent, granula, capsules etc. need to add tensio-active agent or other auxiliary agent usually.In addition The compounds of this invention can with other weedicides such as sterilant, nematocides, sterilant, plant-growth regulator, fertilizer etc. are used with.
The compounds of this invention can be used as single agent or mixture.The preparation method of single agent and mixture sees " Pesticidal FormulationResearch, " (1969), Advances in Chemistry Series No.86, Wade Van Valkenburg; " PesticideFormulations ", (1973) Wade Van Valkenburg.In these single agent and mixture, acceptable inert thinner or tensio-active agent such as solid carrier or liquid vehicle are mixed on the agricultural of activeconstituents and routine.Carrier not only can dissolve, disperse effective constituent but also not influence the activity of effective constituent, and itself does not have the obvious damage effect to soil, equipment, crop or agricultural environment.Auxiliary agent is generally tensio-active agent, stablizer, defoamer or dispersion agent in single agent and the mixture.Single agent of the present invention and mixture comprise that also its purpose is to enlarge the field of activity of preparation and improves drug effect with being mixed of known agricultural chemical compound.
Active constituent content in the preparation (weight percentage) from 0.1% to 99%, and contain at least 0.1% to 20% show activity agent and 1% to 99.9% solid or liquid diluent.
If the compound of general formula I mixes mutually with another weedicide, according to the difference of active compound, application purpose, envrionment conditions and formulation, the content of effective variation range is very big in the mixture.Active constituent content is generally 1% to 95% in the mixture, and suitable content is 5% to 60%.The effective dosage ranges of The compounds of this invention is generally the 1g/ hectare to the 3kg/ hectare, and the 5g/ hectare is better to the 500g/ hectare.
Below with the preparation and examples of formulations the present invention will be described in more detail.But should point out that the present invention never only limits to these concrete examples.In the example of preparation, " part " expression weight percentage, compound number with show 1-25 in consistent.
Preparation example 1 (No. 10 compound)
2-(4-chloro-2-fluoro-5-ethoxycarbonyl methoxy phenyl)-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone 4.0g (being made by the method among the EP0083055A2) and KOH2.1g (85%) stirred 1 hour in 50ml ethanol at ambient temperature, were evaporated to dried then.Add 100ml chloroform and 8ml SOCl in the residuum
2. post-heating refluxed 2 hours.Filter Repone K and wash evaporate to dryness filtrate with fresh chloroform.Add afterwards that 50ml chloroform and 1.5g 1-hydroxymethyl-(1H)-1,2, the 4-triazolo was at room temperature stirring 5 hours.Add water in reaction mixture, tell organic layer and use salt solution Xian Di, dry back concentrates.Residuum gets 2.0g2-(4-chloro-2-fluoro-5-[(1,2,4-triazole methoxyl group)-carbonyl methoxyl group with purification by silica gel column chromatography] phenyl)-4,5,6,7-tetrahydrochysene-2H-isoindole-1, M.P.151-154 ℃ of 3-diketone (No. 10 compound).
Preparation example 2 (No. 26 compound)
2-(4-chloro-2-fluoro-5-hydroxy phenyl)-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone 4.0g (making), 2.0g K by the method among the EP0083055A2
2CO
3With 2.0g chloromethyl-1,2,4-triazolium salt hydrochlorate reflux 5 hours after the cooling, is filtered in the 50ml butanone, and filtrate concentrates.Add water and ethyl acetate in the residuum, tell organic layer, and water and salt water washing, dry back concentrates.Residuum gets 2.6g2-[4-chloro-2-fluoro-5-[(1,2,4-triazole-1H-yl with purification by silica gel column chromatography)-methoxyl group] phenyl]-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone (No. 26 compound) oily matter.
1H?NMR(CDCl
3：8.32(s，1H)，8.01(s，1H)，7.28(d，2H)，7.06(d，2H)，6.04(s，2H)，2.44(bs，4H)，1.83(bs，4H).
Preparation example 3 (No. 484 compound)
The N that contains 0.5g NaH (60%) to 5ml, add 0.8g3-[4-chloro-2-fluoro-5-hydroxy phenyl in the dinethylformamide suspension]-6-trifluoromethyl-2,4-pyrimidone (being made by the method among the EP0255047Al) is after 10 minutes, add 0.8g chloromethyl-1,2,4-triazolium salt hydrochlorate, reaction mixture heated 8 hours in 80 ℃ oil bath, after the cooling, add water and ethyl acetate, tell organic layer and water and salt water washing, dry back concentrates.Residuum gets 0.75g3-[4-chloro-2-fluoro-5-[(1,2,4-triazole-1H-yl with purification by silica gel column chromatography)-methoxyl group] phenyl]-6-trifluoromethyl-2,4-pyrimidone (No. 484 compound), mp.216-219 ℃.
1H NMR (acetone-D
6): 8.64 (s, 1H), 7.96 (s, 1H), 7.55 (d, 2H), 7.52 (d, 2H), 6.36 (s, 1H), 6.27 (s, 2H).
Preparation example 4 (No. 485 compound)
The N that contains 0.8g NaH (60%) to 5ml, add 0.5g3-[4-chloro-2-fluoro-5-[(1 in the dinethylformamide suspension, 2,4-triazole-1H-yl)-methoxyl group]-phenyl]-6-trifluoromethyl-2,4-pyrimidone (compound 484), after 10 minutes, add the 0.2g methyl-sulfate, mixture at room temperature stirs and spends the night.Add water and ethyl acetate in mixture, tell organic layer and water and salt water washing, dry back concentrates.Residuum gets 0.2g 1-methyl-3-[4-chloro-2-fluoro-5-[(1,2,4-triazole-1H-yl with purification by silica gel column chromatography)-methoxyl group] phenyl]-6-trifluoromethyl-2,4-pyrimidone (compound 485).
1H?NMR(CDCl
3)：8.31(s，1H)，7.98(s，1H)，7.36(d，2H)，7.07(d，2H)，6.60(s，1H)，6.06(s，2H)，4.00(s，3H).
Preparation example 5 (No. 773 compound)
2-[4-chloro-2-fluoro-5-[(1,2,4-triazole-1H-yl)-methoxyl group] phenyl]-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone 2.0g and hydrochloric acid 0.7g (36%) stir 10 minutes evaporates to dryness then under the room temperature in 20ml ethanol.Add 5ml acetone in the residuum and stir, filter 1.6g2-[4-chloro-2-fluoro-5-[(1,2,4-triazole-1H-yl) methoxyl group] phenyl]-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-dione hydrochloride (compound 773) solid.
1H?NMR(DMSO-D
6，300MHz)：8.79(s，1H)，8.12(s，1H)，7.70(d，1H)，7.28(d，1H)，6.25(s.2H)，4.96(s，2H)，2.36(bs，4H)，1.75(bs，4H).
Formulation examples 1a-c
50 parts of the 1st, 10 or No. 26 compounds, 5 parts of polyoxyethylene alkane aryl oxides, 5 parts of pelopon A parts, 40 parts of levigate and abundant mixings of artificial hydrated SiO 2 promptly get 50% wettable powder.
Formulation examples 2
10 parts of No. 23 compounds, 6 parts of polyoxyethylene alkane aryl oxides, 4 parts of pelopon As, 30 parts of dimethylbenzene and 50 parts of levigate and abundant mixings of pimelinketone promptly get 10% missible oil.
Formulation examples 3
20 parts of No. 10 compounds, 2 parts of artificial hydrated SiO 2s, 3 parts of the pure monooleates of polyoxyethylene dehydration sorb (sugar), 5 parts of carboxymethyl celluloses are levigate and and 70 parts of abundant mixings of water, and make the effective constituent particle less than 5 microns, promptly get 20% water suspending agent.
Formulation examples 4
5 parts of No. 10 compounds, 1 part of isopropyl acid phosphoric acid salt, 64 parts and 30 parts levigate and abundant mixings of talcum powder of kaolin, and make the effective constituent particle less than 5 microns, promptly get 5% pulvis.
Formulation examples 5
25 parts of No. 10 compounds, 3 parts of the pure monooleates of the rare dehydration sorb of polyoxy second (sugar), 2 parts of polyvinyl alcohols are levigate and and 70 parts of abundant mixings of water, and the effective constituent particle promptly gets 25% water suspending agent less than 5 microns.Biological assay
With weeds Bidens pilosa (beggartick, BID), black nightshade (Solanum nigrum), Polygonum lapathifolium (smartweed, SMT), piemarker (Abutilon theophrasti) and crop such as wheat, corn and soybean are measured this compound.
According to follow procedure each compound is measured.
Measure behind the seedling, seed germination also grew 10-21 days, made the examination material that has a series of growing stages before the processing, selected size, the consistent examination material of growing stage then, handled, and handled to place the greenhouse and water.The examination material with compound treatment does not compare.
Testing compound is with suitable solvent (generally using acetone) dissolving, and its preparation is directly used water dissolution, the processing of spraying then, and spouting liquid is 187 or the 468L/ hectare, dosage is the g/ hectare.2 weeks or the investigation of 4 weeks after processing, with the 0-100 classification, 0 represents non-activity to medicament to each activity of trying material, 100 expressions suppress fully.Partial test the results are shown in Table 26 and 27.
Behind the Table26 compound treatment dosage g/ha BID NS SMT VEL10 seedling behind 150 60 100 40 10026 seedlings 1,200 100 100 100 100
Behind the Table 27 compound treatment dosage g/ha wheat and corn soybean NS10 seedlings behind 150 000 100773 seedlings 150 000 100
Claims (9)
1. the substituted triazole, imidazoles, the pyrazole compound that have weeding activity, shown in general formula I:
Wherein:
R
1Be selected from H, F, Br, Cl, NO
2Or CN;
R
2Be selected from F, Cl, Br, H or CN;
R
3Be selected from H, CN, halogen, alkyl, thiazolinyl, alkynyl, cycloalkyl, cycloalkenyl group, cycloalkenyl group, haloalkyl, haloalkenyl group, halo alkynyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, alkoxyl group, alkylthio, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, the alkyl sulfenyl cycloalkyl, cyano alkoxy, cyano group alkyl, cyano group cycloalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, all these groups can further be replaced;
R
4, R
5Be selected from H respectively, halogen, CN, alkyl, cycloalkyl, haloalkyl, alkoxyl group; alkylthio, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, cyano alkoxy; the cyano group alkyl, cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, CO
2R
6, CONR
6R
13, OR
6, SR
6, SO
2R
6, NR
6R
13, SO
2NR
6R
13, cyano alkoxy, the cyano group alkyl, the cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, aryl, aralkyl or heteroaralkyl, all these groups can further be replaced;
R
6Be selected from H; Alkyl, cycloalkyl, alkoxyl group, alkylthio, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, the alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, cyano alkoxy, the cyano group alkyl, cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, aryl or aralkyl, all these groups can further be replaced;
R
7Be selected from H, alkyl, thiazolinyl, alkynyl, cycloalkyl, alkyl sulfonyl alkyl; the alkyl sulfenyl alkyl, alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl cyano alkoxy, cyano group alkyl, cyano group cycloalkyl; haloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, or COR
9, all these groups can further be replaced;
R
8Be selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl group, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, the alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, cyano alkoxy, the cyano group alkyl, cyano group cycloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, aryl or aralkyl, all these groups can further be replaced;
R
9Be selected from alkyl, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, the alkyl sulfonyl cycloalkyl, alkyl sulfenyl cycloalkyl, thiazolinyl, alkynyl, cyano alkoxy, cyano group alkyl, the cyano group cycloalkyl, haloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl or cycloalkyl, all these groups can further be replaced;
R
10Be selected from H, halogen, NH
2, alkyl, alkyl sulfonyl alkyl, alkyl sulfenyl alkyl, alkyl sulfenyl cycloalkyl, alkyl sulfonyl cycloalkyl, haloalkyl, halogenated alkoxy, halogenated alkylthio, halogenated cycloalkyl, cyano alkoxy, cyano group alkyl, cyano group cycloalkyl, CN, CO
2(alkyl), CONH (alkyl), CON (alkyl)
2, wherein each alkyl is identical or different, CH
2CN, CH
2CH=CH
2, CH
2CCH, CH
2CO
2(alkyl), CH
2OCH
3Or CH
2-1,2, the 4-triazole, all these groups can further be replaced;
R
11Be selected from H, CN, alkyl, haloalkyl or CO
2(alkyl);
R
12Be selected from H, alkyl, CO
2R
6, CONR
6R
13, OR
6, SR
5, SO
2R
6, SO
2NR
6R
13Or NR
6R
13
R
13Be selected from H, alkyl, aryl or aralkyl;
A is selected from N or CH, and B is selected from N or CR
10, have one among A, the B at least and should be N;
Z is selected from O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X can be selected from O, S, NR
12, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (halogen) CO
2, CH
2CH (halogen) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (halogen) CONH or CH
2CH (halogen) CONH:
When Z was O, X can be selected from CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (halogen) CO or CH
2CH (halogen) CO;
When Z is CO, CS, CONR
12Or CSNR
12The time, X can be selected from O, S, CO, OCH (R
6), CH=C (halogen), CH
2CH (halogen), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (halogen) CONH, CH
2CH (halogen) CONH or NR
12
Q is selected from NR
7COR
8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 or Q16 wherein:
Q1 is 4,5,6,7-tetrahydric phthalimide-2-base,
Q2 is 5,6,7,8-tetrahydrochysene-1,2, and 4-triazole [4,3-a] pyridines-3 (2H)-ketone-1-base,
Q3 is 5,6,7,8-tetrahydrochysene-1H, 3H-[1,3,4] thiadiazoles [3,5-a] pyridazine imines-1-base,
Q4 is 4,5,6,7-imidazolidine [1,5-a] pyridine-1,3 (2H, 5H)-diketone-2-base,
Q5 is 1,6,8-three nitrogen dicyclos [4,3,0]-nonane-7, and 9-diketone-8-base,
Q6 is 5-(1-methyl ethylene)-2,4-oxazoline diketone-3-base,
Q7 is 5-(1, the 1-dimethyl ethyl)-1,3,4-oxadiazole-2 (3H)-ketone-3-base,
Q8 is a 4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, and 2,4-triazole-5 (1H)-ketone-1-base,
Q9 is the 2-methyl isophthalic acid, 2, and 4-oxadiazole ketone-3,5-diketone-4-base,
Q10 is 4-chloro-1-methyl-5-difluoro-methoxy-1H-pyrazole-3-yl,
Q11 is 4-bromo-1-methyl-5-Trifluoromethyl-1 H-pyrazole-3-yl,
Q12 is a 1-R10 replacement-6-trifluoromethyl-2,4-pyrimidine dione-3-base,
Q13 is a 1-R10 replacement-6-Trifluoromethyl-1,3, and 5-triazine-2,4-diketone-3-base,
Q14 is 4-R12, and 5-R11-two replaces-4,5-dihydro-1,2, and 4-t triazine-3 (2H)-ketone-2-base,
Q15 is that 4-R10 replaces-1,2, and 4-triazine-3,5 (2H, 4H)-diketone-2-base
Q16 is 5-methyl-6-oxygen-4-(trifluoromethyl)-6H-pyridazine-1-base;
And the salt preparation that can on agricultural, use.
2. according to the described compound of claim 1, it is characterized in that: among the general formula compound I
R
1Be H, F, Br, Cl, NO
2Or CN;
R
2Be F, Cl, Br, H or CN;
R
3Be H, CN, halogen, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulphinyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl basic ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyano group (C
1-C
12) alkoxyl group, cyano group (C
1-C
12) alkyl, cyano group ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkane, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, all these groups all may be undertaken 1-3 time by following radicals and replace, as bromine, and chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or nitro;
R
4And R
5Be H, halogen and CN; (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyano group (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, tooth generation (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, CO
2R
6, CONHR
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, N ((C
1-C
12) a alkyl) R
6, SO
2N ((C
1-C
12) alkyl) R
6, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, all these groups all may be undertaken 1-3 time by following radicals and replace, i.e. bromine, chlorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, a halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-oxane-2-base or nitro;
R
6Be H, (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, aryl or aryl (C
1-C
2) alkyl;
R
7Be H, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl or COR
9
R
8Be (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, ring (C
3-C
8) thiazolinyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, aryl or aryl (C
1-C
12) alkyl;
R
9Be H, (C
1-C
12) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio or halo ring (C
3-C
8) alkyl;
R
10Be H, chlorine, NH
2, (C
1-C
12) alkyl, halo (C
1-C
12) ether, CN, (C
1-C
12) alkyl sulfonyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfenyl (C
1-C
12) alkyl, (C
1-C
12) alkyl sulfonyl ring (C
3-C
8) alkyl, (C
1-C
12) alkyl sulfenyl ring (C
3-C
8) alkyl, cyanogen generation (C
1-C
12) alkoxyl group, cyanogen generation (C
1-C
12) alkyl, cyanogen is for ring (C
3-C
8) alkyl, halo (C
1-C
12) alkoxyl group, halo (C
1-C
12) alkylthio, halo ring (C
3-C
8) alkyl, CO
2(C
1-C
12) alkyl, CONH (C
1-C
12) alkyl, CON ((C
1-C
12) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
12) alkyl, CH
2OCH
3Or CH
2-1,2, the 4-triazole;
R
11Be H, CN, (C
1-C
12) alkyl, halo (C
1-C
12) alkyl or CO
2(C
1-C
12) alkyl;
R
12Be H, (C
1-C
12) alkyl, CO
2R
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, SO
2N ((C
1-C
12) alkyl) R
13Or N ((C
1-C
12) alkyl) R
13
R
13Be H, (C
1-C
12) alkyl, aryl or virtue (C
1-C
12) alkyl;
A is N or CH, and B is N or CR
10, have one among A, the B at least and should be N;
Z is O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X is O, S, NR
12, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (Cl) CO
2, CH
2CH (Cl) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH or CH
2CH (Cl) CONH;
When Z is O, X is CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (Cl) CO or CH
2CH (Cl) CO;
When Z is CO, CS, CONR
12Or CSNR
12, X is O, S, CO, OCH (R
6), CH=C (Cl), CH
2CH (Cl), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH, CH
2CH (Cl) CONH or NR
12
Q is NR
7COR
8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16;
And on agricultural applicable salt preparation.
3. according to the described compound of claim 2, it is characterized in that: among the general formula compound I
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, bromine, chlorine, fluorine, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
6) alkynyl, halo (C
1-C
6) alkyl, halo (C
2-C
6) thiazolinyl, halo (C
2-C
6) alkynyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, aryl, heteroaryl, virtue (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, wherein aryl or heteroaryl are furans, naphthalene, and phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole, aryl and heteroaryl can be undertaken 1-3 time by following radicals and replace, as bromine, chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or ammonia;
R
4And R
5Be H, bromine, chlorine, fluorine, CN, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
6) alkyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, CO
2R
6, CONHR
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, N ((C
1-C
12) alkyl) R
6, SO
2N ((C
1-C
12) alkyl) R
6, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, wherein aryl or heteroaryl are furans, naphthalene, and phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole it is reported that aryl and heteroaryl may be undertaken 1-3 time by following radicals and replace, as bromine, chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
2) alkoxyl group, 1,3-diox-2-base or nitro;
R
6Be H, (C
1-C
12) alkyl, aryl or aryl (C
1-C
6) alkyl, wherein aryl is naphthyl or phenyl;
R
7Be H, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl or COR
9
R
8Be (C
1-C
12) alkyl, halo (C
3-C
8) alkyl, ring (C
3-C
8) thiazolinyl, halo (C
1-C
12) alkyl, aryl or aryl (C
1-C
6) alkyl;
R
9Be H, (C
1-C
6) alkyl, (C
2-C
12) thiazolinyl, (C
2-C
6) alkynyl, ring (C
3-C
8) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
12) alkyl;
R
10Be H, chlorine, NH
2, (C
1-C
6) alkyl, halo (C
1-C
12) alkyl, CN, CO
2(C
1-C
12) alkyl, CONH (C
1-C
12) alkyl, CON ((C
1-C
12) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
12) alkyl, CH
2OCH
3Or CH
2-1,2, the 4-triazole;
R
3Be H, bromine, chlorine, fluorine, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
6) alkynyl, halo (C
1-C
6) alkyl, halo (C
2-C
6) thiazolinyl, halo (C
2-C
6) alkynyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, aryl, heteroaryl, virtue (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, wherein aryl or heteroaryl are furans, naphthalene, and phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole, aryl and heteroaryl can be undertaken 1-3 time by following radicals and replace, as bromine, chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or ammonia;
R
4And R
5Be H, bromine, chlorine, fluorine, CN, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
6) alkyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, CO
2R
6, CONHR
6, CON ((C
1-C
12) alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, N ((C
1-C
12) alkyl) R
6, SO
2N ((C
1-C
12) alkyl) R
6, aryl, heteroaryl, aryl (C
1-C
12) alkyl and heteroaryl (C
2-C
12) alkyl, wherein aryl or heteroaryl are furans, naphthalene, and phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole it is reported that aryl and heteroaryl may be undertaken 1-3 time by following radicals and replace, as bromine, chlorine, fluorine, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, (C
2-C
12) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
12) alkynyl, halo (C
1-C
12) alkyl, halo (C
2-C
12) thiazolinyl, halo (C
2-C
12) alkynyl, (C
1-C
12) alkoxyl group, (C
1-C
12) alkylthio, (C
1-C
12) alkyl sulphonyl, (C
1-C
12) alkyl sulphinyl, phenyl, benzene generation (C
1-C
12) alkyl, benzene generation (C
2-C
12) thiazolinyl, benzene generation (C
2-C
12) alkynyl, cyano group, halo (C
1-C
12) alkoxyl group, 1,3-diox-2-base or nitro:
R
6Be H, (C
1-C
12) alkyl, aryl or aryl (C
1-C
6) alkyl, wherein aryl is naphthyl or phenyl;
R
7Be H, (C
1-C
12) alkyl, ring (C
3-C
8) alkyl, halo (C
1-C
12) alkyl or COR
9
R
8Be (C
1-C
12) alkyl, halo (C
3-C
8) alkyl, ring (C
3-C
8) thiazolinyl, halo (C
1-C
12) alkyl, aryl or aryl (C
1-C
6) alkyl;
R
9Be H, (C
1-C
6) alkyl, (C
2-C
12) thiazolinyl, (C
2-C
6) alkynyl, ring (C
3-C
8) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
12) alkyl;
R
10Be H, chlorine, NH
2, (C
1-C
6) alkyl, halo (C
1-C
12) alkyl, CN, CO
2(C
1-C
12) alkyl, CONH (C
1-C
12) alkyl, CON ((C
1-C
12) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
12) alkyl, CH
2OQH
3Or CH
2-1,2, the 4-triazole;
R
11Be H, CN, (C
1-C
6) alkyl, halo (C
1-C
12) alkyl, halo (C
1-C
6) alkyl, CO
2(C
1-C
12) alkyl:
R
12Be H, (C
1-C
8) alkyl, CO
2R
6, CON ((C
1-C
8) alkyl) R
6, OR
6, SR
6, SO
2R
6, SO
2N ((C
1-C
8) alkyl) R
13Or N ((C
1-C
8) alkyl) R
13
R
13Be H, (C
1-C
8) alkyl, aryl (C
1-C
6) alkyl, wherein aryl is naphthyl or phenyl;
A is N or CH, and B is N or CR
10, have one among A, the B at least and should be N;
Z is O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X is O, S, NH, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (Cl) CO
2, CH
2CH (Cl) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH or CH
2CH (Cl) CONH;
When Z was O, X was CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (Cl) CO or CH
2CH (Cl) CO;
When Z is CO, CS, CONR
12Or CSNR
12, X is O, S, CO, OCH (R
6), CH=C (Cl), CH
2CH (Cl), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH, CH
2CH (Cl) CONH or NR
12
Q is NR
7COR
8, or Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 or Q16;
And by hydrochloric acid, sulfuric acid, acetate, propionic acid, the formed salt preparation that can on agricultural, use of phosphoric acid or oxalic acid.
4, according to the described compound of claim 3, it is characterized in that: among the general formula compound I
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, bromine, chlorine, fluorine, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
3-C
8) thiazolinyl, (C
2-C
6) alkynyl, halo (C
1-C
6) alkyl, halo (C
2-C
6) thiazolinyl, halo (C
2-C
6) alkynyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-two chloro-3-furyls, 1-naphthyl, 2-naphthyl, phenyl, 4-methylbenzene, 4-p-methoxy-phenyl, the 4-nitrophenyl, 4-fluorophenyl, 4-chloro-phenyl-, the 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l, 4-benzonitrile base, 3-(1,3-diox-2-yl) phenyl, the 2-fluorophenyl, the 2-chloro-phenyl-, 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3, the 5-dichlorophenyl, the 2,4 difluorobenzene base, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-chloro-5-trifluoromethyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-two chloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-two chloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxyl group-4-pyridyl, 2-cyanogen-4-pyridyl, 2,6-two fluoro-4-pyridyl, 2,6-two chloro-4-pyridyl, the 2-thienyl, the 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-two chloro-3-thienyls;
R
4And R
5Be H, bromine, chlorine, fluorine, CN, (C
1-C
6) alkyl, cyanogen generation (C
5-C
6) alkyl, halo (C
1-C
6) alkyl, (C
1-C
6) alkoxyl group, (C
1-C
6) alkylthio, CO
2R
6, CONHR
6, CON ((C
1-C
6) alkyl) R
6, OR
6, SR
6, SO
2R
6, NHR
6, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-two chloro-3-furyls, 1-naphthyl, 2-naphthyl, phenyl, 4-tolyl, 4-p-methoxy-phenyl, the 4-nitrophenyl, 4-fluorophenyl, 4-chloro-phenyl-, the 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l 4-benzonitrile base, 3-(1,3-diox-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-fluoro-5-Trifluoromethoxyphen-l, 3,4, the 5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-two chloro-2-pyridyl, the 3-pyridyl, 5-bromo-3-pyridyl 1,5,6-two chloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, the 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxyl group-4-pyridyl, 2-cyanogen-4-pyridyl, 2,6-two fluoro-4-pyridyl 2,6-two chloro-4-pyridyl, the 2-thienyl, the 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-two chloro-3-three thienyls;
R
6Be H, (C
1-C
6) alkyl, 1-naphthyl, 2-naphthyl, phenyl, the 4-aminomethyl phenyl, 4-p-methoxy-phenyl, 4-nitrophenyl, 4-fluorophenyl, the 4-chloro-phenyl-, 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l, 4-cyanogen are for phenyl, and 3-(1,3-diox-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chlorine 4-fluorophenyl, 3, the 4-difluorophenyl, 3-fluoro-5-trifluoromethyl or 3,4, the 5-trifluorophenyl;
R
7Be H, (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
6) alkyl or COR
9
R
8Be (C
1-C
6) alkyl, ring (C
5-C
6) alkyl, halo (C
1-C
12) alkyl, 1-naphthyl, 2-naphthyl, phenyl, the 4-aminomethyl phenyl, 4-p-methoxy-phenyl, 4-nitrophenyl, 4-fluorophenyl, the 4-chloro-phenyl-, 4-trifluoromethyl, 4-bromophenyl, 3-chloro-phenyl-, the 3-fluorophenyl, the 4-Trifluoromethoxyphen-l, 4-benzonitrile base, 3-(1,3-diox-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, 2-Trifluoromethoxyphen-l, 3,5-difluorophenyl, 3,5-dichlorophenyl; The 2,4 difluorobenzene base, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-chloro-5-trifluoromethyl or 3,4,5-trifluorophenyl;
R
9Be H, (C
1-C
6) alkyl, (C
2-C
6) thiazolinyl, ring (C
5-C
6) alkyl or halo (C
1-C
6) alkyl;
R
10Be H,, NH
2, (C
1-C
6) alkyl, halo (C
1-C
6) alkyl, CN, CO
2(C
1-C
6) alkyl, CONH (C
1-C
6) alkyl, CON ((C
1-C
6) alkyl)
2, CH
2CN, CH
2CH=CH
2, CH
2C ≡ CH, CH
2CO
2(C
1-C
6) alkyl, CH
2OCH
3Or CH
2-1,2, the 4-triazole;
R
11Be H, CN, (C
1-C
6) alkyl, halo (C
1-C
6) alkyl or CO
2(C
1-C
6) alkyl;
R
12Be H, (C
1-C
8) alkyl, CO
2(C
1-C
6) alkyl, CON ((C
1-C
6) alkyl)
2, O (C
1-C
6) alkyl, S (C
1-C
6) alkyl, SO
2(C
1-C
6) alkyl, SO
2N ((C
1-C
6) alkyl)
2Or N ((C
1-C
6) alkyl)
2
R
13Be H, (C
1-C
6) alkyl, aryl or aryl (C
1-C
4) alkyl, wherein aryl is naphthyl or phenyl;
A is N or CH, and B is N or CR
10, have one among A, the B at least and should be N;
Z is O, CH (R
3), CO, CS, CONR
12Or CSNR
12
When Z is CH (R
3) time, X is O, S, NH, CO
2, OCH (R
6) CO
2, SCH (R
6) CO
2, CH=C (Cl) CO
2, CH
2CH (Cl) CO
2, CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH or CH
2CH (Cl) CONH;
When Z was O, X was CO, OCH (R
6) CO, SCH (R
6) CO, CH=C (Cl) CO or CH
2CH (Cl) CO;
When Z is CO, CS, CONR
12Or CSNR
12The time, X is O, S, CO, OCH (R
6), CH=C (Cl), CH
2CH (Cl), CONH, OCH (R
6) CONH, SCH (R
6) CONH, CH=C (Cl) CONH, CH
2CH (Cl) CONH or NR
12
Q is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 or Q16; And by hydrochloric acid, acetate, the prepared salt preparation that can on agricultural, use of phosphoric acid or oxalic acid.
5, a kind of herbicidal composition is characterized in that: the active ingredient in the said composition is the compound described in the claim 1, and the content of active ingredient is 0.1% to 99%.
6, according to the described herbicidal composition of claim 5, it is characterized in that: also contain agricultural in the composition and go up applicable carrier.
7, according to the described herbicidal composition of claim 5, it is characterized in that: the agricultural chemicals or the fertilizer that can also contain other in the said composition.
8, the method for a kind of management of weeds is characterized in that: weeds, weed growth ground or weed growth medium to farm crop Tanaka are used herbicidal composition as claimed in claim 5.
9, according to the method for the described management of weeds of claim 6, it is characterized in that: farm crop are wheat, corn and soybean.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00110501 CN1118465C (en) | 2000-06-08 | 2000-06-08 | Substituted triazole, imidazole or pyrazole herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00110501 CN1118465C (en) | 2000-06-08 | 2000-06-08 | Substituted triazole, imidazole or pyrazole herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1327984A true CN1327984A (en) | 2001-12-26 |
| CN1118465C CN1118465C (en) | 2003-08-20 |
Family
ID=4580489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 00110501 Expired - Fee Related CN1118465C (en) | 2000-06-08 | 2000-06-08 | Substituted triazole, imidazole or pyrazole herbicides |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1118465C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7754880B2 (en) * | 2002-12-23 | 2010-07-13 | Isagro Ricerca S.R.L. | Uracils having a herbicidal activity |
| DE102006015704B4 (en) | 2006-04-04 | 2018-07-19 | Skw Stickstoffwerke Piesteritz Gmbh | New 1,2-bis (azol-1-yl) ethane-1,2-diols as intermediates for the synthesis of agrochemicals and process for their preparation |
-
2000
- 2000-06-08 CN CN 00110501 patent/CN1118465C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7754880B2 (en) * | 2002-12-23 | 2010-07-13 | Isagro Ricerca S.R.L. | Uracils having a herbicidal activity |
| DE102006015704B4 (en) | 2006-04-04 | 2018-07-19 | Skw Stickstoffwerke Piesteritz Gmbh | New 1,2-bis (azol-1-yl) ethane-1,2-diols as intermediates for the synthesis of agrochemicals and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1118465C (en) | 2003-08-20 |
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