CN1033132C - Method for killing weeds - Google Patents
Method for killing weeds Download PDFInfo
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- CN1033132C CN1033132C CN 92102225 CN92102225A CN1033132C CN 1033132 C CN1033132 C CN 1033132C CN 92102225 CN92102225 CN 92102225 CN 92102225 A CN92102225 A CN 92102225A CN 1033132 C CN1033132 C CN 1033132C
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- alkyl group
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- pyrimidine derivatives
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Abstract
A pyrimidine derivative having the formula (I) wherein X is a halogen atom, a lower alkyl group or a phenoxy group (wherein said phenoxy group may be substituted by halogen, lower alkyl or lower alkoxy), and R is a hydrogen atom, a lower alkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, an alkoxycarbonyl alkyl group, a cyanoalkyl group or a <CHEM> group (wherein R<1> is a hydrogen atom or a lower alkyl group, and R<2> is a lower alkyl group or a phenyl group which may be substituted by nitro), or a salt thereof.
Description
The present invention relates to the herbicidal methods of Noval pyrimidine derivatives or its salt and these materials of use.
Recently, developed large quantities of weed killer herbicides and be used for practice, weed killer herbicide is to save the energy of agricultural operation and improve the efficient of producing to contribute.In addition, known various 2-phenoxy pyrimidine derivates are effective [(1) Japanese laid-open publications 174059/1987, (2) Japanese laid-open publication 55729/1979 and (3) agricultural biochemistry 30 are rolled up 896 pages (1966) No. 9] as weed killer herbicide.
Yet disclosed compound in above-mentioned list of references (1) although they demonstrate efficient herbicidal effect, has individual safety issue to crops.In addition, the deficiency of disclosed compound is that its activity of weeding to annual careless class is not enough in above-mentioned list of references (2) and (3), and the perennial grass class is not demonstrated significant activity of weeding yet.
The present inventor has carried out extensive studies to develop a kind of compound with more excellent activity of weeding to pyrimidine derivatives, found that the compound of introducing substituent at the pyrimidine and the ad-hoc location on the phenyl ring of phenyl sulphur pyrimidine derivatives of the present invention demonstrates excellent herbicidal effect to perennial grass class and annual careless class, simultaneously, they are to crops, particularly, has tight security for cotton.Of the present invention finishing is based on these discoveries.
Pyrimidine derivatives provided by the invention has general expression:
Wherein X is the halogen atom such as chlorine, bromine, iodine or fluorine, low alkyl group, particularly C
1-C
4Alkyl, or phenoxy group (wherein said phenoxy group can be by the halogen atom such as chlorine, bromine, iodine or fluorine, low alkyl group, particularly C
1-C
4Alkyl replaces, or lower alkoxy, particularly C
1-C
4Alkoxyl replaces), R is a halogen atom, low alkyl group, particularly C
1-C
4Alkyl, alkoxyalkyl, particularly C
1-C
4Alkoxy C
1-C
4Alkyl, benzyloxy alkyl, particularly benzyloxy C
1-C
4Alkyl, alkoxycarbonyl alkyl, particularly C
1-C
4Alkoxy carbonyl group C
1-C
4Alkyl, the cyano group alkyl or
Group (R wherein
1Be hydrogen atom or low alkyl group, particularly C
1-C
4Alkyl, R
2Be low alkyl group, particularly C
1-C
4Alkyl or the phenyl that can be replaced by nitro), perhaps be its salt.
The invention provides the method for weeding, this method comprises that pyrimidine derivatives or its salt of the molecular formula I of the effective dose with herbicide effect are applied to the place that will administer.
Now describe the present invention in detail with object lesson preferably.
In molecular formula I, X replaces in the 6-position, and particularly X is chlorine atom, methyl or the fluorine atom in the 6-position.
R is preferably hydrogen atom, low alkyl group, alkoxyalkyl or benzyloxy alkyl.Best is hydrogen atom.
In the compound of molecular formula I, be preferably following general expression I-1 and I-2.
Wherein defined in R such as the claim 1, X is halogen atom or low alkyl group;
Wherein defined in R such as the claim 1, Y is hydrogen atom, halogen atom, low alkyl group or lower alkoxy.
Now the object lesson of The compounds of this invention is listed in table 1.The numbering of the compound of being given in the table is corresponding with the description order in the specification.
Table 1
Table 1 (continuing)
Table 1 (continuing)
In compound of the present invention, benzoic acid derivative (R wherein is a hydrogen atom) or its salt demonstrate excellent especially herbicidal effect.
Salt can be alkali metal salt, alkali salt, transition metal salt or organic ammonium salt.
Be numbered 1,2,11,12,17,18,21 compound and salt pair crop, particularly cotton are superior especially having aspect excellent activity of weeding and the no obvious phytotoxicity.
Herbicidal combinations of the present invention comprises that it has herbicidally effective amount, such as, 0.5% to 95% weight portion is the The compounds of this invention and the agricultural agent of 1 to 80% weight portion preferably.Weed killer herbicide of the present invention can use separately, or is made into different preparations, such as, wetting powder, granule, and missible oil or be equipped with carrier, surfactant, dispersant or be generally used for the pulvis of the auxiliary agent of agricultural chemicals preparation.
The carrier that is used for preparation can be such as Jeeklite, talcum, bentonite, clay, kaolin, diatomite, white carbon black, vermiculite, white lime, silica sand, the solid carrier of ammonium sulfate or urea etc.; Such as isopropyl alcohol, dimethylbenzene, the liquid-carrier of cyclohexane or methyl naphthalene etc.Surfactant described here and dispersant can be pure sulphonic acid esters, alkyl aryl sulfonate, lignosulfonates, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether or polyoxyethylene sorbitol mono alkyl ester.Auxiliary agent can be carboxymethyl cellulose, polyethylene glycol or gum Arabic.
In actual use, this weed killer herbicide can be diluted to suitable concentration before use, or can directly use.Weed killer herbicide of the present invention also can be used in combination with other weed killer herbicides.
Weed killer herbicide of the present invention carried out the surface irrigation dispenser or passed through foliage application the green bristlegrass grass in the paddy field before or after germinateing at the green bristlegrass grass.In addition, when weed killer herbicide of the present invention puts on nonirrigated farmland or non-agricultural crop field, can before or after germinateing, the green bristlegrass grass carry out area spray or foliage application.
For area spray, the dosage that applies of weed killer herbicide of the present invention is that per 10 are of 1 gram is to 1 kilogram of active component.For foliage application, it is diluted to 1 to 10, the concentration of 000ppm applies with the dosage of per 10 are of 1 gram to 1 kilogram of active component.
Now provide the formulation examples of herbicidal composition of the present invention, but should be understood that the present invention is not only limited in these specific examples." % " expression percentage by weight in these examples.
Formulation examples 1 (wetting powder)
Be numbered 1 compound with 10%, 0.5%Emulgen 810 (trade marks, Kao company), 0.5%Demol N (trade mark, Kao company), 20% Kunilite 201 (trade mark, Kunimine Kogyo company) and 69% Jeeklite CA (trade mark, Jeeklite Co., Ltd) mixes also pulverize equably, obtain wetting powder.
Formulation examples 2 (missible oil)
Be numbered 1 compound with 30%, 20% cyclohexane, 11% polyoxyethylene alkylaryl ether, 4% alkyl benzene calcium sulfonate and 35% methyl naphthalene uniform dissolution obtain missible oil.
Formulation examples 3 (granule)
Be numbered 1 compound with 5%; 2% laruyl alcohol-sulphonic acid ester sodium salt; 5% sodium lignin sulfonate; 2% carboxymethyl cellulose and 86% clay evenly mix and pulverize; get this mixture of 100 weight portions and add 20 weight parts waters; this mixture of kneading is extruded into 14 to 32 purpose particles with comminutor, and drying obtains pellet again.
Formulation examples 4 (pulvis)
Be numbered 2 compound with 2%, 5% diatomite and 93% clay evenly mix and pulverize, obtain pulvis.
Compound of the present invention and herbicidal composition can control effectively long in paddy field such as barnyard grass (Echinochloa crus-galli), nutgrass flatsedge (Cyperus difformis), Monochoria korsakowii annual grass such as (Monchoria vaginalis); And such as Fischer grass genus (Scirpushotarui), wear the leaf rhizoma alismatis, the nutgrass flatsedge (Cyperus serotinus) that spend on evening, the perennial grass of short arrowhead (Sagittaria pygmaea) and water chestnut (Eleocharis Kurogwai) etc.In addition, also can control effectively long dry land such as barnyard grass (Echinochloa crus-galli), lady's-grass (Digitaria sanguinalis), yard grass (Eleusine indica), green foxtail (Sefaria viridis), water foxtail (Alopecurus aequalis), annual precocious dogstail (Poa annua), wild oat (Avena fatua), Italian ryegrass (Lolium multi-form), arsesmart (polygonum Capathifolium), thin amaranth (Amaranthusviridis), lamb's-quarters (Chenopodium album), velvetleaf (Abutilon theophrasti), thorniness bur (Sida spinosa), Cassia tora (Cassia tora), chickweed (Stellarta media), morning glory (lpomoea spp), common Siberian cocklebur (Xanthiumstrumarium) paddy nutgrass flatsedge (Cyperus iria), wide leaf arm shape grass (Brachiariaplatphylla), Rottboellia exaltata (Rotloboellia exaltata), pubescence bromegrass (Bromus tectorum), RHIZOMA FAGOPYRI CYMOSI (Polygonum convolvulus), the annual grass of wild cruciate flower (Brassica arvensis) and shirt rim beggar-ticks (Bidens frondosa) etc.; And such as Murex purpurea nutgrass flatsedge (Cyperus rotundus), Johnson grass (Sorghumhalepense), the perennial grass of Bermuda grass (Cynodon dactylon) and quackgrass (Agropyron repens) etc.On the other hand, to crops, cotton particularly, its safety is high.
When weed killer herbicide of the present invention is used as the cotton weed killer herbicide, have following characteristics; In addition, when it is used as the weed killer herbicide of the crops except that cotton, various advantages are arranged equally.
In every kind of application method of the foliage application after (1) area spray of weed killer herbicide of the present invention before grass germinates germinates with grass, be high safety for cotton.Correspondingly, weed killer herbicide of the present invention can be used as the cotton weed killer herbicide of the foliage application after the preceding area spray of grass germination germinates with grass.
(2) weed killer herbicide of the present invention has herbicide effect to the green bristlegrass grass that makes us feeling a delicacy about such as common Siberian cocklebur and morning glory, and before grass germinates to the germination over a long time in be effective.
(3) weed killer herbicide of the present invention has suitably decomposability in earth, and contiguous crops are not had obvious facilitation.
The activity of weeding of weed killer herbicide of the present invention is now described with test examples.Test examples 1 (the area spray method before grass germinates in the nonirrigated farmland)
(surface area 600cm in a basin earth
2), sow cotton (Go), barnyard grass (Ec), Johnson grass (So), arsesmart (Po), thin amaranth (Am), lamb's-quarters (Ch), the seed of morning glory (Ip) and common Siberian cocklebur (Xa); The stem tuber of Murex purpurea nutgrass flatsedge (Cr) under kind; Cover the thick earth of one deck 0.5 to 1cm again.Sowing one day after, the wetting powder dilute with water that the method in the formulation examples 1 of scheduled volume is made also is applied to earth surfaces with per 10 ares 100 liters ratio.Measured in the 20th day after dispenser, and being defined as standard evaluation gained result in the table 2, and index was listed in table 3 and table 4.
Table 2
| Index | Herbicidal effect and phytotoxicity |
| 0 1 2 3 4 5 | No herbicidal effect (or plant-less toxicity) herbicidal effect (or phytotoxicity) greater than 0% less than 30% herbicidal effect (or phytotoxicity) be at least 30% and less than 50% herbicidal effect (or phytotoxicity) be at least 50% and less than 70% herbicidal effect (or phytotoxicity) be at least 70% and less than 90% herbicidal effect (or phytotoxicity) greater than 90% |
Table 3
| Compound number | Active constituent dosage (gai/10a) | Phytotoxicity | Herbicidal effect | |||||||
| Go | Ec | So | Po | Am | Ch | Ip | Xa | Cr | ||
| 1 2 | 100 25 100 25 | 0 0 0 0 | 5 4 5 3 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 3 0 | 5 5 4 3 | 5 5 5 4 |
| Contrast compound 1 | 100 25 | 3 2 | 5 4 | 5 5 | 5 5 | 5 5 | 5 5 | 3 0 | 2 0 | 4 3 |
Control compounds 1 as give a definition (being equally applicable in other tables):
Control compounds 1:2-[(4,6-dimethoxypyridin-2-yl) oxo] benzoic acid (disclosed in Japanese laid-open publication 174059/1987)
Table 4
Test examples 2 (foliage application method after grass germinates in the nonirrigated farmland)
| Compound number | Active constituent dosage (gai/10a) | Phytotoxicity | Herbicidal effect | |||||||
| Go | Ec | So | Po | Am | Ch | Ip | Xa | Cr | ||
| 10 11 12 13 14 17 18 21 24 25 27 28 | 25 100 25 100 25 100 100 100 25 100 25 100 25 25 25 100 25 100 25 | 1 1 0 0 0 1 1 1 0 1 0 0 0 1 1 1 0 0 0 | 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 4 4 3 5 5 5 3 5 5 5 5 5 3 5 5 5 5 5 4 | 3 4 2 5 4 5 3 5 5 5 5 4 2 5 4 5 4 5 4 | 5 5 5 5 5 5 4 5 5 5 4 5 5 5 5 5 5 5 5 |
| Control compounds 1 | 100 25 | 3 3 | 5 4 | 5 4 | 5 5 | 5 5 | 5 5 | 2 0 | 2 0 | 4 2 |
(surface area is 600cm in a basin mud
2) sow cotton (Go), barnyard grass (Ec), Johnson grass (So), arsesmart (Po), thin amaranth (Am), lamb's-quarters (Ch), the seed of morning glory (Ip) and common Siberian cocklebur (Xa) is planted the stem tuber of Murex purpurea nutgrass flatsedge (Cr) down; Cover the thick earth of one deck 0.5 to 1cm again.This basin was cultivated for 2 weeks in 20 to 25 ℃ greenhouse, and then, the wetting powder dilute with water by the preparation of the method in the formulation examples 1 with scheduled volume puts on the blade with 100 liters every are ratios.Measured in the 14th day after the dispenser, and being defined as standard evaluation gained result in the table 2, and index was listed in table 5 and table 6.
Table 5
| Compound number | Active constituent dosage (gai/10a) | Phytotoxicity | Herbicidal effect | |||||||
| Go | Ec | So | Po | Am | Ch | Ip | Xa | Cr | ||
| 1 2 | 100 25 100 25 | 1 0 1 0 | 5 4 5 3 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 4 3 | 5 5 5 4 | 5 5 5 5 |
| Control compounds 1 | 100 25 | 5 4 | 5 5 | 5 5 | 5 5 | 5 5 | 5 5 | 3 1 | 3 2 | 4 3 |
Table 6
Test examples 3 (the foliage application method in the nonirrigated farmland)
| Compound number | Active constituent dosage (gai/10a) | Phytotoxicity | Herbicidal effect | |||||||
| Go | Ec | So | Po | Am | Ch | Ip | Xa | Cr | ||
| 24 25 27 29 | 25 25 25 25 | 0 0 0 0 | 4 4 4 4 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 | 5 5 5 5 |
| Control compounds 1 | 25 | 4 | 5 | 4 | 5 | 5 | 5 | 1 | 1 | 2 |
(surface area is 100cm in a basin earth
2), sow barnyard grass (Ec), lady's-grass (Di), arsesmart (Po), the seed of thin amaranth (Am) lamb's-quarters (Ch) and paddy nutgrass flatsedge (Ci) covers with the thick earth of one deck 0.5 to 1cm again.Basin was cultivated for 2 weeks in 20 to 25 ℃ greenhouse, with the wetting powder dilute with water by the preparation of the method in the formulation examples 1 of scheduled volume, put on the blade then with per 10 ares 100 liters ratios.Measure with the 14th day after the herbicide treatment, being defined as standard evaluation gained result in the table 2, and index is listed in table 7 and table 8.
Table 7
| Compound number | Herbicidal effect | |||||
| Ec | Di | Po | Am | Ch | Ci | |
| 1 2 | 5 5 | 5 5 | 5 5 | 5 5 | 5 5 | 5 5 |
| Control compounds 1 control compounds 2 control compounds 3 control compounds 4 | 5 0 1 1 | 5 1 1 1 | 4 2 2 1 | 5 2 1 1 | 5 0 1 1 | 5 5 5 1 |
Table 8
| Compound number | Herbicidal effect | |||||
| Ec | Di | Po | Am | Ch | Ci | |
| 3 10 11 12 13 14 16 17 18 21 24 25 26 27 28 29 31 32 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 |
| Control compounds 2 control compounds 3 control compounds 4 | 0 1 1 | 1 1 0 | 2 2 1 | 1 1 1 | 1 1 1 | 5 5 1 |
Control compounds 2,3 and 4 is as give a definition (being equally applicable in the table)
Control compounds 2: oxo ethyl-3-[(5-Chloropyrimide-2-yl)] benzoic ether (disclosed in the Japanese laid-open publication 55729/1979),
Control compounds 3: oxo ethyl-5[(5-Chloropyrimide-2-yl)]-2-nitrobenzoyl acid esters (disclosed in the Japanese laid-open publication 55729/1979)
Control compounds 4:2-(2-toloxyl-4,6-dimethyl pyrimidine) agricultural and biochemistry, 30 volumes, No. 9, disclosed in 896 pages) test examples 4 (area spray method in the nonirrigated farmland)
(surface area is 100cm in a basin earth
2), sow barnyard grass (Ec), lady's-grass (Di), arsesmart (Po), thin amaranth (Am), the seed of lamb's-quarters (Ch) and paddy nutgrass flatsedge (Ci), and cover the thick earth of one deck 0.5 to 1cm.Sow after one day,, and put on the surface (dosage of active constituent is 100g/10a) of earth with per 10 ares 100 liters ratio the wetting powder dilute with water by the preparation of the method in the formulation examples 1 of scheduled volume.Measured in the 20th day after the dispenser, and being defined as standard evaluation gained result in the table 2, and index was listed in table 9 and table 10.
Table 9
| Compound number | Herbicidal effect | |||||
| Ec | Di | Po | Am | Ch | Ci | |
| 1 2 | 5 5 | 5 5 | 5 5 | 5 5 | 5 5 | 5 5 |
| Control compounds 1 control compounds 2 control compounds 3 control compounds 4 | 5 0 0 0 | 5 0 0 0 | 4 0 0 0 | 5 0 0 0 | 5 0 2 0 | 5 5 5 0 |
Table 10
| Compound number | Herbicidal effect | |||||
| Ec | Di | Po | Am | Ch | Ci | |
| 3 4 5 6 7 9 10 11 12 13 14 16 17 18 21 22 23 24 25 26 27 28 29 31 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 |
| Control compounds 2 control compounds 3 control compounds 4 | 0 0 0 | 0 0 0 | 0 0 0 | 0 0 0 | 0 2 0 | 5 4 0 |
Test examples 5 (test of control green bristlegrass grass in the paddy field)
In a basin paddy field earth, sow barnyard grass (Ec), nutgrass flatsedge (Cd), Monochoria korsakowii (Mo) and common rush (Sc) seed, it is dark to add water to 3cm.Sow after 2 days,, and drop to water surface with the dosage of per 10 are of 100 gram active constituent with the wetting powder dilute with water by the preparation of the method in the formulation examples 1 of scheduled volume.Measured in the 21st day after the dispenser, and being defined as standard evaluation gained result in the table 2, and index was listed in table 11 and table 12.
Table 11
| Compound number | Herbicidal effect |
| Ec Cd Mo Sc | |
| 1 2 | 5 5 5 5 5 5 5 5 |
Table 12
| Compound number | Herbicidal effect |
| Ec Cd Mo Sc | |
| 3 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 | 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 |
Claims (8)
1. the method for a killing weeds is characterized in that it comprises molecular formula is that the pyrimidine derivatives with herbicidally effective amount or its salt of I puts on the place that will administer,
X is a halogen atom in the formula (I), low alkyl group or phenoxy group, and wherein said phenoxy group can be replaced by halogen atom, low alkyl group or lower alkoxy; R is a hydrogen atom, low alkyl group, alkoxyalkyl, benzyloxy alkyl, alkoxy carbonyl alkyl, cyanoalkyl or
Base, wherein R
1Be hydrogen atom or low alkyl group, R
2Be the low alkyl group or the phenyl that can be replaced by nitro, the alkyl in wherein said alkoxyalkyl, benzyloxy alkyl, alkoxy carbonyl alkyl or the cyanoalkyl is low alkyl group.
2. the method for claim 1 is characterized in that R is a hydrogen atom in the pyrimidine derivatives of formula (I), low alkyl group, alkoxyalkyl or benzyloxy alkyl.
3. the method for claim 1 is characterized in that the molecular formula of wherein said pyrimidine derivatives or its salt is (I-1)
Wherein R such as claim 1 are defined, and X is halogen atom or low alkyl group.
4. the method for claim 1, the salt that it is characterized in that pyrimidine derivatives is alkali metal salt, alkali salt, transition metal salt or organic ammonium salt.
5. the method for claim 1 is characterized in that the molecular formula of wherein said pyrimidine derivatives or its salt is (I-2)
Wherein R such as claim 1 are defined, and Y is a hydrogen atom, halogen atom, low alkyl group or lower alkoxy.
6. the method for claim 1 is characterized in that the R in the pyrimidine derivatives of formula (I) is a hydrogen atom
7. the method for claim 1 is characterized in that the pyrimidine derivatives described in the pyrimidine derivatives of formula (I) is 2-chloro-6-((4,6-dimethoxypyridin-2-yl) sulfo-) benzoic acid or its salt.
8. the method for claim 1 is characterized in that the X in the pyrimidine derivatives of formula (I) is chlorine atom, methyl or the fluorine atom of 6-position.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27889487 | 1987-11-04 | ||
| JP278894/87 | 1987-11-04 | ||
| CN88107663A CN1025981C (en) | 1987-11-04 | 1988-11-04 | Pyrimidine derivatives, processes for their production and herbicidal method and compositions |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88107663A Division CN1025981C (en) | 1987-11-04 | 1988-11-04 | Pyrimidine derivatives, processes for their production and herbicidal method and compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1064586A CN1064586A (en) | 1992-09-23 |
| CN1033132C true CN1033132C (en) | 1996-10-30 |
Family
ID=25742504
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 92102225 Expired - Lifetime CN1033132C (en) | 1987-11-04 | 1992-03-26 | Method for killing weeds |
| CN 92102226 Expired - Lifetime CN1028171C (en) | 1987-11-04 | 1992-03-26 | Process for producing pyrimidine derivative or salt thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 92102226 Expired - Lifetime CN1028171C (en) | 1987-11-04 | 1992-03-26 | Process for producing pyrimidine derivative or salt thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN1033132C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101279950B (en) * | 2007-04-06 | 2010-08-11 | 中国中化股份有限公司 | 2-pyrimindinyloxy (pyrimindinylthio) benzoxy acetamide compound and application thereof |
| CN103039454B (en) * | 2013-01-22 | 2014-12-03 | 南京高正农用化工有限公司 | Pyrithiobac sodium-paraquat weeding composition and application thereof |
-
1992
- 1992-03-26 CN CN 92102225 patent/CN1033132C/en not_active Expired - Lifetime
- 1992-03-26 CN CN 92102226 patent/CN1028171C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1028171C (en) | 1995-04-12 |
| CN1064586A (en) | 1992-09-23 |
| CN1065862A (en) | 1992-11-04 |
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