CA1072556A - 5-pyrimidinecarbonitriles a proprietes herbicides - Google Patents

5-pyrimidinecarbonitriles a proprietes herbicides

Info

Publication number: CA1072556A
Authority: CA; Canada
Prior art keywords: amino; pyrimidinecarbonitrile; cyano; isopropylamino; methoxy
Prior art date: 1976-08-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA284,585A

Other languages

English (en)

Inventor

Gino R. Treves

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FMC Corp

Original Assignee

FMC Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-08-27

Filing date

1977-08-12

Publication date

1980-02-26

1977-06-30 Priority claimed from US05/811,917 external-priority patent/US4092150A/en

1977-08-12 Application filed by FMC Corp filed Critical FMC Corp

1980-02-26 Application granted granted Critical

1980-02-26 Publication of CA1072556A publication Critical patent/CA1072556A/fr

Status Expired legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 35
150000001875 compounds Chemical class 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 20
230000008635 plant growth Effects 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
-1 isopropylamino Chemical group 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 22
241000196324 Embryophyta Species 0.000 claims description 18
125000003282 alkyl amino group Chemical group 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 15
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims description 10
230000012010 growth Effects 0.000 claims description 7
AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 claims description 6
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
GHPANXXDQMHDBH-UHFFFAOYSA-N 2,4-diamino-6-chloropyrimidine-5-carbonitrile Chemical compound NC1=NC(N)=C(C#N)C(Cl)=N1 GHPANXXDQMHDBH-UHFFFAOYSA-N 0.000 claims description 4
240000008042 Zea mays Species 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
UGPXXWQEKARQTD-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbonitrile Chemical compound NC1=NC(Cl)=C(C#N)C(Cl)=N1 UGPXXWQEKARQTD-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000006317 cyclopropyl amino group Chemical group 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
244000299507 Gossypium hirsutum Species 0.000 claims description 2
235000007244 Zea mays Nutrition 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
JVKQWXNWRNZYDT-UHFFFAOYSA-N 2-(2-cyanopropan-2-ylamino)-4-methoxy-6-(propan-2-ylamino)pyrimidine-5-carbonitrile Chemical compound COC1=NC(NC(C)(C)C#N)=NC(NC(C)C)=C1C#N JVKQWXNWRNZYDT-UHFFFAOYSA-N 0.000 claims 4
RKTGRIAFCPYGAI-UHFFFAOYSA-N 2-(2-cyanopropan-2-ylamino)-4-(cyclopropylamino)-6-methoxypyrimidine-5-carbonitrile Chemical compound COC1=NC(NC(C)(C)C#N)=NC(NC2CC2)=C1C#N RKTGRIAFCPYGAI-UHFFFAOYSA-N 0.000 claims 3
DUZNEAGKNLVPJX-UHFFFAOYSA-N 2-(2-cyanopropan-2-ylamino)-4-(ethylamino)-6-methoxypyrimidine-5-carbonitrile Chemical compound CCNC1=NC(NC(C)(C)C#N)=NC(OC)=C1C#N DUZNEAGKNLVPJX-UHFFFAOYSA-N 0.000 claims 3
WHOYVSQXYWBSLY-UHFFFAOYSA-N 1-ethyl-2-propan-2-ylhydrazine Chemical group CCNNC(C)C WHOYVSQXYWBSLY-UHFFFAOYSA-N 0.000 claims 1
244000105624 Arachis hypogaea Species 0.000 claims 1
235000010777 Arachis hypogaea Nutrition 0.000 claims 1
244000068988 Glycine max Species 0.000 claims 1
235000010469 Glycine max Nutrition 0.000 claims 1
235000009432 Gossypium hirsutum Nutrition 0.000 claims 1
240000006394 Sorghum bicolor Species 0.000 claims 1
235000011684 Sorghum saccharatum Nutrition 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 29
239000000543 intermediate Substances 0.000 abstract description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
229940022682 acetone Drugs 0.000 description 10
239000004009 herbicide Substances 0.000 description 10
238000004458 analytical method Methods 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000002689 soil Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
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239000007787 solid Substances 0.000 description 4
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 3
IFWYZASANXAZHN-UHFFFAOYSA-N 4-chloro-2,6-bis(ethylamino)pyrimidine-5-carbonitrile Chemical compound CCNC1=NC(Cl)=C(C#N)C(NCC)=N1 IFWYZASANXAZHN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
208000037974 severe injury Diseases 0.000 description 3
230000009528 severe injury Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
IAJCAZVXGKGAQK-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC(Cl)=C(C#N)C(Cl)=N1 IAJCAZVXGKGAQK-UHFFFAOYSA-N 0.000 description 2
LDKSFTHTVGJVGY-UHFFFAOYSA-N 4,6-dichloro-2-(propan-2-ylamino)pyrimidine-5-carbonitrile Chemical compound CC(C)NC1=NC(Cl)=C(C#N)C(Cl)=N1 LDKSFTHTVGJVGY-UHFFFAOYSA-N 0.000 description 2
GPSJXTNDEKZOLA-UHFFFAOYSA-N 4-chloro-6-(cyclopropylamino)-2-(propan-2-ylamino)pyrimidine-5-carbonitrile Chemical compound CC(C)NC1=NC(Cl)=C(C#N)C(NC2CC2)=N1 GPSJXTNDEKZOLA-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
240000008415 Lactuca sativa Species 0.000 description 2
235000003228 Lactuca sativa Nutrition 0.000 description 2
235000010617 Phaseolus lunatus Nutrition 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
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238000001914 filtration Methods 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
SDGUCCSEUGQHDP-UHFFFAOYSA-N 2,4-bis(ethylamino)-6-methoxypyrimidine-5-carbonitrile Chemical compound CCNC1=NC(NCC)=C(C#N)C(OC)=N1 SDGUCCSEUGQHDP-UHFFFAOYSA-N 0.000 description 1
ZQOUBVWOXICZTH-UHFFFAOYSA-N 2,4-bis(ethylamino)-6-propan-2-yloxypyrimidine-5-carbonitrile Chemical compound CCNC1=NC(NCC)=C(C#N)C(OC(C)C)=N1 ZQOUBVWOXICZTH-UHFFFAOYSA-N 0.000 description 1
VULZVYGZVOMUKU-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carboxamide Chemical class NC(=O)C1=CN=C(N)N=C1N VULZVYGZVOMUKU-UHFFFAOYSA-N 0.000 description 1
MWHRWDHXMLXSIB-UHFFFAOYSA-N 2-(butan-2-ylamino)-4,6-dichloropyrimidine-5-carbonitrile Chemical compound CCC(C)NC1=NC(Cl)=C(C#N)C(Cl)=N1 MWHRWDHXMLXSIB-UHFFFAOYSA-N 0.000 description 1
MEQLPKJXHCUDAW-UHFFFAOYSA-N 2-(butan-2-ylamino)-4-methoxy-6-(propan-2-ylamino)pyrimidine-5-carbonitrile Chemical compound CCC(C)NC1=NC(NC(C)C)=C(C#N)C(OC)=N1 MEQLPKJXHCUDAW-UHFFFAOYSA-N 0.000 description 1
YCNZNDXXSHKISX-UHFFFAOYSA-N 2-(diethylamino)-4-methoxy-6-(methylamino)pyrimidine-5-carbonitrile Chemical compound CCN(CC)C1=NC(NC)=C(C#N)C(OC)=N1 YCNZNDXXSHKISX-UHFFFAOYSA-N 0.000 description 1
HXGGECADMGCAOE-UHFFFAOYSA-N 2-(ethylamino)-4-methoxy-6-(methylamino)pyrimidine-5-carbonitrile Chemical compound CCNC1=NC(NC)=C(C#N)C(OC)=N1 HXGGECADMGCAOE-UHFFFAOYSA-N 0.000 description 1
JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-UHFFFAOYSA-N 0.000 description 1
QLIYACYNFPXHHX-UHFFFAOYSA-N 2-amino-4-(ethylamino)-6-methoxypyrimidine-5-carbonitrile Chemical compound CCNC1=NC(N)=NC(OC)=C1C#N QLIYACYNFPXHHX-UHFFFAOYSA-N 0.000 description 1
CJKJPYVWWSQGBI-UHFFFAOYSA-N 2-amino-4-methoxy-6-(propan-2-ylamino)pyrimidine-5-carbonitrile Chemical compound COC1=NC(N)=NC(NC(C)C)=C1C#N CJKJPYVWWSQGBI-UHFFFAOYSA-N 0.000 description 1
AQWHMZLJILFROC-UHFFFAOYSA-N 2-amino-4-methoxypyrimidine-5-carbonitrile Chemical compound COC1=NC(N)=NC=C1C#N AQWHMZLJILFROC-UHFFFAOYSA-N 0.000 description 1
125000004892 2-methylpropylamino group Chemical group CC(CN*)C 0.000 description 1
IPEBKIMUIHKZJP-UHFFFAOYSA-N 4,6-dichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC=NC(Cl)=C1C#N IPEBKIMUIHKZJP-UHFFFAOYSA-N 0.000 description 1
LEKAYNOZNQNGFK-UHFFFAOYSA-N 4-(cyclopropylamino)-6-methoxy-2-(propan-2-ylamino)pyrimidine-5-carbonitrile Chemical compound COC1=NC(NC(C)C)=NC(NC2CC2)=C1C#N LEKAYNOZNQNGFK-UHFFFAOYSA-N 0.000 description 1
CBBQGIBNEQJEHR-UHFFFAOYSA-N 4-chloro-2-(2-cyanopropan-2-ylamino)-6-(cyclopropylamino)pyrimidine-5-carbonitrile Chemical compound N#CC(C)(C)NC1=NC(Cl)=C(C#N)C(NC2CC2)=N1 CBBQGIBNEQJEHR-UHFFFAOYSA-N 0.000 description 1
FSVHRJVWYCRBMM-UHFFFAOYSA-N 4-chloro-2-(2-cyanopropan-2-ylamino)-6-(ethylamino)pyrimidine-5-carbonitrile Chemical compound CCNC1=NC(NC(C)(C)C#N)=NC(Cl)=C1C#N FSVHRJVWYCRBMM-UHFFFAOYSA-N 0.000 description 1
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OTKHBGUGRNLPKZ-UHFFFAOYSA-N 6-hydroxy-2,4-dioxo-1h-pyrimidine-5-carboxamide Chemical compound NC(=O)C1=C(O)NC(=O)NC1=O OTKHBGUGRNLPKZ-UHFFFAOYSA-N 0.000 description 1
241000209764 Avena fatua Species 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
241000219198 Brassica Species 0.000 description 1
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244000178993 Brassica juncea Species 0.000 description 1
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244000045232 Canavalia ensiformis Species 0.000 description 1
208000018380 Chemical injury Diseases 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
235000017896 Digitaria Nutrition 0.000 description 1
241001303487 Digitaria <clam> Species 0.000 description 1
235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
235000017898 Digitaria ciliaris Nutrition 0.000 description 1
235000005476 Digitaria cruciata Nutrition 0.000 description 1
235000006830 Digitaria didactyla Nutrition 0.000 description 1
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
244000025670 Eleusine indica Species 0.000 description 1
235000014716 Eleusine indica Nutrition 0.000 description 1
102100039856 Histone H1.1 Human genes 0.000 description 1
101001035402 Homo sapiens Histone H1.1 Proteins 0.000 description 1
241001527806 Iti Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
244000100170 Phaseolus lunatus Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
238000007059 Strecker synthesis reaction Methods 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
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238000006073 displacement reaction Methods 0.000 description 1
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239000000194 fatty acid Substances 0.000 description 1
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QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
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Plural Heterocyclic Compounds (AREA)

CA284,585A 1976-08-27 1977-08-12 5-pyrimidinecarbonitriles a proprietes herbicides Expired CA1072556A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US71822476A	1976-08-27	1976-08-27
US05/811,917 US4092150A (en)	1976-08-27	1977-06-30	Herbicidal 5-pyrimidinecarbonitriles

Publications (1)

Publication Number	Publication Date
CA1072556A true CA1072556A (fr)	1980-02-26

Family

ID=27109863

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA284,585A Expired CA1072556A (fr)	1976-08-27	1977-08-12	5-pyrimidinecarbonitriles a proprietes herbicides

Country Status (12)

Country	Link
JP (1)	JPS5328185A (fr)
BR (1)	BR7705708A (fr)
CA (1)	CA1072556A (fr)
DE (1)	DE2738653A1 (fr)
DK (1)	DK379577A (fr)
EG (1)	EG12928A (fr)
FR (1)	FR2362842A1 (fr)
GB (1)	GB1548348A (fr)
IL (1)	IL52748A0 (fr)
IT (1)	IT1086509B (fr)
LU (1)	LU78040A1 (fr)
NL (1)	NL7709393A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4783468A (en) *	1986-04-30	1988-11-08	Ciba-Geigy Corporation	Insecticidal 5-pyrimidine carbonitriles
DE19917785A1 (de) *	1999-04-20	2000-10-26	Bayer Ag	2,4-Diamino-pyrimidin-Derivate

1977
- 1977-08-12 CA CA284,585A patent/CA1072556A/fr not_active Expired
- 1977-08-16 IL IL52748A patent/IL52748A0/xx unknown
- 1977-08-25 NL NL7709393A patent/NL7709393A/xx not_active Application Discontinuation
- 1977-08-25 FR FR7725945A patent/FR2362842A1/fr active Pending
- 1977-08-25 GB GB35733/77A patent/GB1548348A/en not_active Expired
- 1977-08-26 JP JP10178977A patent/JPS5328185A/ja active Pending
- 1977-08-26 LU LU78040A patent/LU78040A1/xx unknown
- 1977-08-26 DK DK379577A patent/DK379577A/da unknown
- 1977-08-26 IT IT27016/77A patent/IT1086509B/it active
- 1977-08-26 DE DE19772738653 patent/DE2738653A1/de not_active Withdrawn
- 1977-08-26 BR BR7705708A patent/BR7705708A/pt unknown
- 1977-08-27 EG EG500/77A patent/EG12928A/xx active

Also Published As

Publication number	Publication date
NL7709393A (nl)	1978-03-01
IL52748A0 (en)	1977-10-31
JPS5328185A (en)	1978-03-16
LU78040A1 (fr)	1978-04-27
DK379577A (da)	1978-02-28
FR2362842A1 (fr)	1978-03-24
BR7705708A (pt)	1978-05-16
IT1086509B (it)	1985-05-28
DE2738653A1 (de)	1978-03-02
GB1548348A (en)	1979-07-11
EG12928A (en)	1980-07-31

Legal Events

Date	Code	Title	Description
1997-02-26	MKEX	Expiry

Publication	Publication Date	Title
JP2558516B2 (ja)	1996-11-27	ピリミジン誘導体及び除草剤
CA1119182A (fr)	1982-03-02	Derives de l'acide phenoxy-phenoxypropionique
US4684398A (en)	1987-08-04	Herbicidal cyanoguanidines and cyanoisothioureas
US4979982A (en)	1990-12-25	Herbicidal cinnamic ester uracils
US4927451A (en)	1990-05-22	3-aryldihydrouracils
US4383850A (en)	1983-05-17	Benzthiazole or benzoxazole ethers, herbicidal compositions and use
CA1307275C (fr)	1992-09-08	Derives quinoxaline et composition herbicide
JPS5827770B2 (ja)	1983-06-11	除草剤
CA1148958A (fr)	1983-06-28	Derives d'acide 4-oxyphenoxyalcane carboxylique, heterocyclique, substitue
DD231716A5 (de)	1986-01-08	Herbizide mittel
AU608244B2 (en)	1991-03-28	4-substituted-2,6-diphenylpyridine derivatives, production of the same, and herbicide containing the same as an active ingredient
US4626273A (en)	1986-12-02	Herbicidal novel 2-alkoxyaminosulfonyl-benzene-sulfonylureas
US4723986A (en)	1988-02-09	Herbicidal oxazolidines and methods of use
US4531966A (en)	1985-07-30	Herbicide compositions
JPS6092277A (ja)	1985-05-23	置換フエノキシアルカンカルボン酸エステル，その製法及び除草剤
US4092150A (en)	1978-05-30	Herbicidal 5-pyrimidinecarbonitriles
EP0062254A1 (fr)	1982-10-13	Acétanilides substitués, procédé pour leur préparation et leur utilisation comme herbicides
US4627870A (en)	1986-12-09	Certain phenoxy-benzamido-diphenyl-phosphonate esters having herbicidal activity
US3383195A (en)	1968-05-14	m-(3, 3-dimethylureido) phenyl dimethyl-sulfamate as a herbicide
USRE31136E (en)	1983-02-01	Herbicidal 5-pyrimidinecarbonitriles
DD156664A5 (de)	1982-09-15	Herbizide und den pflanzenwuchs hemmende mittel
US4714491A (en)	1987-12-22	Diphenyl ether herbicides
EP0057367A1 (fr)	1982-08-11	2-Pyridyloxyacétanilides, procédé pour leur préparation et leur utilisation
US4554014A (en)	1985-11-19	O-Aryloxyphenoxyacyl-α-N,N,-dialkylaminooximes and herbicidal methods of use
US3714162A (en)	1973-01-30	New herbicidal n-(1-cycloalken-1-yl)-amino-s-triazine compounds